diff --git a/components/ClientEmailSection.vue b/components/ClientEmailSection.vue
new file mode 100644
index 0000000..68ae514
--- /dev/null
+++ b/components/ClientEmailSection.vue
@@ -0,0 +1,425 @@
+<template>
+  <div>
+    <v-card-title class="text-h6 d-flex align-center pb-4">
+      <v-icon class="mr-2" color="primary">mdi-email</v-icon>
+      Email Communication
+    </v-card-title>
+    <v-card-text class="pt-0">
+      
+      <!-- Compose New Email -->
+      <div class="mb-4">
+        <v-btn
+          @click="showComposer = true"
+          color="primary"
+          variant="flat"
+          prepend-icon="mdi-email-edit"
+        >
+          Compose Email
+        </v-btn>
+      </div>
+
+      <!-- Email Thread List -->
+      <div v-if="emailThreads.length > 0" class="email-threads">
+        <div class="text-subtitle-1 mb-3">Email History</div>
+        <v-timeline side="end" density="comfortable">
+          <v-timeline-item
+            v-for="(email, index) in emailThreads"
+            :key="index"
+            :dot-color="email.direction === 'sent' ? 'primary' : 'success'"
+            :icon="email.direction === 'sent' ? 'mdi-email-send' : 'mdi-email-receive'"
+            size="small"
+          >
+            <template v-slot:opposite>
+              <div class="text-caption">
+                {{ formatDate(email.timestamp) }}
+              </div>
+            </template>
+            
+            <v-card variant="outlined">
+              <v-card-subtitle class="d-flex align-center">
+                <span class="text-body-2">
+                  {{ email.direction === 'sent' ? 'To' : 'From' }}: 
+                  {{ email.direction === 'sent' ? email.to : email.from }}
+                </span>
+              </v-card-subtitle>
+              
+              <v-card-text>
+                <div class="text-body-2 font-weight-medium mb-2">{{ email.subject }}</div>
+                <div class="email-content" v-html="formatEmailContent(email.content)"></div>
+                
+                <!-- Attachments -->
+                <div v-if="email.attachments && email.attachments.length > 0" class="mt-3">
+                  <v-chip
+                    v-for="(attachment, i) in email.attachments"
+                    :key="i"
+                    size="small"
+                    color="primary"
+                    variant="tonal"
+                    prepend-icon="mdi-paperclip"
+                    class="mr-2"
+                  >
+                    {{ attachment.name }}
+                  </v-chip>
+                </div>
+              </v-card-text>
+            </v-card>
+          </v-timeline-item>
+        </v-timeline>
+      </div>
+      
+      <!-- Empty State -->
+      <div v-else class="text-center py-8 text-grey">
+        <v-icon size="48" class="mb-3">mdi-email-outline</v-icon>
+        <div>No email communication yet</div>
+      </div>
+    </v-card-text>
+
+    <!-- Email Composer Dialog -->
+    <v-dialog v-model="showComposer" max-width="800" persistent>
+      <v-card>
+        <v-card-title class="d-flex align-center">
+          <v-icon class="mr-2">mdi-email-edit</v-icon>
+          Compose Email
+          <v-spacer />
+          <v-btn icon="mdi-close" variant="text" @click="closeComposer"></v-btn>
+        </v-card-title>
+        
+        <v-divider />
+        
+        <v-card-text>
+          <!-- Recipient Info -->
+          <v-alert type="info" variant="tonal" class="mb-4">
+            <div class="d-flex align-center">
+              <v-icon class="mr-2">mdi-account</v-icon>
+              <div>
+                <div class="font-weight-medium">{{ interest['Full Name'] }}</div>
+                <div class="text-caption">{{ interest['Email Address'] }}</div>
+              </div>
+            </div>
+          </v-alert>
+
+          <!-- Subject -->
+          <v-text-field
+            v-model="emailDraft.subject"
+            label="Subject"
+            variant="outlined"
+            density="comfortable"
+            class="mb-4"
+          />
+
+          <!-- Quick Actions -->
+          <div class="mb-3">
+            <span class="text-body-2 mr-2">Quick Insert:</span>
+            <v-btn
+              v-if="hasEOI"
+              @click="insertEOILink"
+              size="small"
+              variant="tonal"
+              prepend-icon="mdi-file-document"
+            >
+              EOI Link
+            </v-btn>
+            <v-btn
+              @click="insertFormLink"
+              size="small"
+              variant="tonal"
+              prepend-icon="mdi-form-select"
+              class="ml-2"
+            >
+              Interest Form
+            </v-btn>
+            <v-btn
+              v-if="hasBerth"
+              @click="insertBerthInfo"
+              size="small"
+              variant="tonal"
+              prepend-icon="mdi-anchor"
+              class="ml-2"
+            >
+              Berth Info
+            </v-btn>
+          </div>
+
+          <!-- Email Content -->
+          <v-textarea
+            v-model="emailDraft.content"
+            label="Email Content"
+            variant="outlined"
+            rows="12"
+            placeholder="Write your email here..."
+            ref="contentTextarea"
+          />
+
+          <!-- Attachments -->
+          <v-file-input
+            v-model="emailDraft.attachments"
+            label="Attachments"
+            variant="outlined"
+            density="comfortable"
+            multiple
+            chips
+            prepend-icon="mdi-paperclip"
+            class="mt-4"
+          />
+        </v-card-text>
+        
+        <v-divider />
+        
+        <v-card-actions>
+          <v-spacer />
+          <v-btn @click="closeComposer" variant="text">Cancel</v-btn>
+          <v-btn
+            @click="sendEmail"
+            color="primary"
+            variant="flat"
+            prepend-icon="mdi-send"
+            :loading="isSending"
+          >
+            Send Email
+          </v-btn>
+        </v-card-actions>
+      </v-card>
+    </v-dialog>
+  </div>
+</template>
+
+<script setup lang="ts">
+import type { Interest } from '~/utils/types';
+
+const props = defineProps<{
+  interest: Interest;
+}>();
+
+const emit = defineEmits<{
+  'email-sent': [];
+  'update': [];
+}>();
+
+const toast = useToast();
+const showComposer = ref(false);
+const isSending = ref(false);
+const emailThreads = ref<any[]>([]);
+const contentTextarea = ref<any>(null);
+
+const emailDraft = ref<{
+  subject: string;
+  content: string;
+  attachments: File[];
+}>({
+  subject: '',
+  content: '',
+  attachments: []
+});
+
+// Check if interest has EOI or berth
+const hasEOI = computed(() => {
+  const eoiDocs = props.interest['EOI Document'];
+  const hasEOIDocs = Array.isArray(eoiDocs) && eoiDocs.length > 0;
+  return !!(props.interest['Signature Link Client'] || hasEOIDocs);
+});
+
+const hasBerth = computed(() => {
+  const berths = props.interest.Berths;
+  const hasBerthsArray = Array.isArray(berths) && berths.length > 0;
+  return !!(hasBerthsArray || props.interest['Berth Number']);
+});
+
+// Load email thread on mount
+onMounted(() => {
+  loadEmailThread();
+});
+
+// Watch for interest changes
+watch(() => props.interest.Id, () => {
+  loadEmailThread();
+});
+
+const loadEmailThread = async () => {
+  try {
+    const response = await $fetch<{
+      success: boolean;
+      emails: any[];
+    }>('/api/email/fetch-thread', {
+      method: 'POST',
+      headers: {
+        'x-tag': '094ut234'
+      },
+      body: {
+        email: props.interest['Email Address']
+      }
+    });
+    
+    if (response.success) {
+      emailThreads.value = response.emails || [];
+    }
+  } catch (error) {
+    console.error('Failed to load email thread:', error);
+  }
+};
+
+const insertEOILink = () => {
+  if (!contentTextarea.value) return;
+  
+  const link = props.interest['Signature Link Client'] || 
+               props.interest['EOI Client Link'] ||
+               'EOI document has been generated for your review';
+  
+  const insertText = `\n\nPlease review and sign your Expression of Interest (EOI) document:\n${link}\n\n`;
+  
+  insertAtCursor(insertText);
+};
+
+const insertFormLink = () => {
+  const formLink = `https://form.portnimara.com/interest/${props.interest.Id}`;
+  const insertText = `\n\nPlease complete your interest form:\n${formLink}\n\n`;
+  
+  insertAtCursor(insertText);
+};
+
+const insertBerthInfo = () => {
+  let berthNumber = props.interest['Berth Number'];
+  
+  // Check if Berths is an array and has items
+  if (!berthNumber && Array.isArray(props.interest.Berths) && props.interest.Berths.length > 0) {
+    berthNumber = props.interest.Berths[0]['Berth Number'];
+  }
+  
+  const insertText = `\n\nBerth Information:\nBerth Number: ${berthNumber || 'TBD'}\n\n`;
+  
+  insertAtCursor(insertText);
+};
+
+const insertAtCursor = (text: string) => {
+  const textarea = contentTextarea.value.$el.querySelector('textarea');
+  if (!textarea) return;
+  
+  const start = textarea.selectionStart;
+  const end = textarea.selectionEnd;
+  const current = emailDraft.value.content;
+  
+  emailDraft.value.content = current.substring(0, start) + text + current.substring(end);
+  
+  // Set cursor position after inserted text
+  nextTick(() => {
+    textarea.focus();
+    textarea.setSelectionRange(start + text.length, start + text.length);
+  });
+};
+
+const sendEmail = async () => {
+  if (!emailDraft.value.subject || !emailDraft.value.content) {
+    toast.error('Please enter a subject and message');
+    return;
+  }
+  
+  isSending.value = true;
+  
+  try {
+    // Format email content with proper line breaks
+    const formattedContent = emailDraft.value.content
+      .split('\n')
+      .map(line => line.trim() ? `<p>${line}</p>` : '<br>')
+      .join('');
+    
+    // Prepare email data
+    const emailData = {
+      to: props.interest['Email Address'],
+      toName: props.interest['Full Name'],
+      subject: emailDraft.value.subject,
+      html: formattedContent,
+      interestId: props.interest.Id.toString()
+    };
+    
+    // Send email
+    const response = await $fetch<{
+      success: boolean;
+      messageId?: string;
+    }>('/api/email/send', {
+      method: 'POST',
+      headers: {
+        'x-tag': '094ut234'
+      },
+      body: emailData
+    });
+    
+    if (response.success) {
+      toast.success('Email sent successfully');
+      
+      // Add to thread
+      emailThreads.value.unshift({
+        direction: 'sent',
+        to: props.interest['Email Address'],
+        subject: emailDraft.value.subject,
+        content: formattedContent,
+        timestamp: new Date().toISOString(),
+        attachments: emailDraft.value.attachments.map((f: File) => ({ name: f.name }))
+      });
+      
+      // Close composer and reset
+      closeComposer();
+      emit('email-sent');
+      emit('update');
+    }
+  } catch (error: any) {
+    console.error('Failed to send email:', error);
+    toast.error(error.data?.statusMessage || 'Failed to send email');
+  } finally {
+    isSending.value = false;
+  }
+};
+
+const closeComposer = () => {
+  showComposer.value = false;
+  // Reset draft
+  emailDraft.value = {
+    subject: '',
+    content: '',
+    attachments: []
+  };
+};
+
+const formatDate = (dateString: string) => {
+  if (!dateString) return '';
+  
+  const date = new Date(dateString);
+  return date.toLocaleString('en-GB', {
+    day: '2-digit',
+    month: '2-digit',
+    year: 'numeric',
+    hour: '2-digit',
+    minute: '2-digit'
+  });
+};
+
+const formatEmailContent = (content: string) => {
+  // Ensure HTML content is properly formatted
+  if (content.includes('<p>') || content.includes('<br>')) {
+    return content;
+  }
+  // Convert plain text to HTML
+  return content.split('\n').map(line => `<p>${line}</p>`).join('');
+};
+</script>
+
+<style scoped>
+.email-content {
+  max-height: 200px;
+  overflow-y: auto;
+  line-height: 1.6;
+}
+
+.email-content :deep(p) {
+  margin: 0 0 0.5em 0;
+}
+
+.email-content :deep(br) {
+  display: block;
+  content: "";
+  margin: 0.5em 0;
+}
+
+.email-threads {
+  max-height: 600px;
+  overflow-y: auto;
+}
+</style>
diff --git a/components/EOISection.vue b/components/EOISection.vue
index d431787..30809fb 100644
--- a/components/EOISection.vue
+++ b/components/EOISection.vue
@@ -5,9 +5,31 @@
       EOI Management
     </v-card-title>
     <v-card-text class="pt-0">
-    
-      <!-- Generate EOI Button -->
-      <div v-if="!hasEOI" class="mb-4">
+      
+      <!-- EOI Documents Section -->
+      <div v-if="hasEOIDocuments" class="mb-4">
+        <div class="text-subtitle-1 mb-2">EOI Documents</div>
+        <div class="d-flex flex-wrap ga-2">
+          <v-chip
+            v-for="(doc, index) in eoiDocuments"
+            :key="index"
+            color="primary"
+            variant="tonal"
+            prepend-icon="mdi-file-pdf-box"
+            :href="doc.url"
+            target="_blank"
+            component="a"
+            clickable
+            closable
+            @click:close="removeDocument(index)"
+          >
+            {{ doc.title || `EOI Document ${index + 1}` }}
+          </v-chip>
+        </div>
+      </div>
+      
+      <!-- Generate EOI Button - Only show if no documents uploaded -->
+      <div v-if="!hasEOI && !hasEOIDocuments" class="mb-4">
         <v-btn
           @click="generateEOI"
           :loading="isGenerating"
@@ -18,6 +40,18 @@
           Generate EOI
         </v-btn>
       </div>
+      
+      <!-- Upload EOI Button -->
+      <div class="mb-4">
+        <v-btn
+          @click="showUploadDialog = true"
+          variant="outlined"
+          prepend-icon="mdi-upload"
+          :disabled="isUploading"
+        >
+          {{ hasEOI ? 'Upload Signed EOI' : 'Upload EOI Document' }}
+        </v-btn>
+      </div>
 
       <!-- EOI Status Badge -->
       <div v-if="hasEOI" class="mb-4 d-flex align-center">
@@ -100,6 +134,37 @@
         </v-btn>
       </div>
     </v-card-text>
+    
+    <!-- Upload Dialog -->
+    <v-dialog v-model="showUploadDialog" max-width="500">
+      <v-card>
+        <v-card-title>Upload EOI Document</v-card-title>
+        <v-card-text>
+          <v-file-input
+            v-model="selectedFile"
+            label="Select EOI document (PDF)"
+            accept=".pdf"
+            prepend-icon="mdi-file-pdf-box"
+            variant="outlined"
+            density="comfortable"
+            :rules="[v => !!v || 'Please select a file']"
+          />
+        </v-card-text>
+        <v-card-actions>
+          <v-spacer />
+          <v-btn @click="showUploadDialog = false">Cancel</v-btn>
+          <v-btn
+            color="primary"
+            variant="flat"
+            @click="handleUpload"
+            :loading="isUploading"
+            :disabled="!selectedFile"
+          >
+            Upload
+          </v-btn>
+        </v-card-actions>
+      </v-card>
+    </v-dialog>
   </div>
 </template>
 
@@ -115,8 +180,11 @@ const emit = defineEmits<{
   'update': [];
 }>();
 
-const { showToast } = useToast();
+const toast = useToast();
 const isGenerating = ref(false);
+const showUploadDialog = ref(false);
+const isUploading = ref(false);
+const selectedFile = ref<File | null>(null);
 
 const hasEOI = computed(() => {
   return !!(props.interest['Signature Link Client'] || 
@@ -124,7 +192,15 @@ const hasEOI = computed(() => {
            props.interest['Signature Link Developer']);
 });
 
-const generateEOI = async () => {
+const eoiDocuments = computed(() => {
+  return props.interest['EOI Document'] || [];
+});
+
+const hasEOIDocuments = computed(() => {
+  return eoiDocuments.value.length > 0;
+});
+
+const generateEOI = async (retryCount = 0) => {
   isGenerating.value = true;
   
   try {
@@ -144,16 +220,27 @@ const generateEOI = async () => {
     });
     
     if (response.success) {
-      showToast(response.documentId === 'existing' 
+      toast.success(response.documentId === 'existing' 
         ? 'EOI already exists - signature links retrieved' 
         : 'EOI generated successfully');
       
       emit('eoi-generated', { signingLinks: response.signingLinks });
       emit('update'); // Trigger parent to refresh data
+    } else {
+      throw new Error('EOI generation failed');
     }
   } catch (error: any) {
     console.error('Failed to generate EOI:', error);
-    showToast(error.data?.statusMessage || 'Failed to generate EOI');
+    
+    // Retry logic
+    if (retryCount < 3) {
+      console.log(`Retrying EOI generation... Attempt ${retryCount + 2}/4`);
+      await new Promise(resolve => setTimeout(resolve, (retryCount + 1) * 1000));
+      return generateEOI(retryCount + 1);
+    }
+    
+    // Show error message after all retries failed
+    toast.error(error.data?.statusMessage || error.message || 'Failed to generate EOI after multiple attempts');
   } finally {
     isGenerating.value = false;
   }
@@ -164,7 +251,7 @@ const copyLink = async (link: string | undefined) => {
   
   try {
     await navigator.clipboard.writeText(link);
-    showToast('Signature link copied to clipboard');
+    toast.success('Signature link copied to clipboard');
     
     // Update EOI Time Sent if not already set
     if (!props.interest['EOI Time Sent']) {
@@ -187,7 +274,7 @@ const copyLink = async (link: string | undefined) => {
       }
     }
   } catch (error) {
-    showToast('Failed to copy link');
+    toast.error('Failed to copy link');
   }
 };
 
@@ -225,4 +312,45 @@ const getStatusColor = (status: string) => {
       return 'grey';
   }
 };
+
+const removeDocument = async (index: number) => {
+  // For now, we'll just show a message since removing documents 
+  // would require updating the database
+  toast.warning('Document removal is not yet implemented');
+};
+
+const uploadEOI = async (file: File) => {
+  isUploading.value = true;
+  
+  try {
+    const formData = new FormData();
+    formData.append('file', file);
+    
+    const response = await $fetch<{ success: boolean; document: any; message: string }>('/api/eoi/upload-document', {
+      method: 'POST',
+      query: {
+        interestId: props.interest.Id.toString()
+      },
+      body: formData
+    });
+    
+    if (response.success) {
+      toast.success('EOI document uploaded successfully');
+      showUploadDialog.value = false;
+      selectedFile.value = null; // Reset file selection
+      emit('update'); // Refresh parent data
+    }
+  } catch (error: any) {
+    console.error('Failed to upload EOI:', error);
+    toast.error(error.data?.statusMessage || 'Failed to upload EOI document');
+  } finally {
+    isUploading.value = false;
+  }
+};
+
+const handleUpload = () => {
+  if (selectedFile.value) {
+    uploadEOI(selectedFile.value);
+  }
+};
 </script>
diff --git a/components/EmailComposer.vue b/components/EmailComposer.vue
index 3974d5e..d73a352 100644
--- a/components/EmailComposer.vue
+++ b/components/EmailComposer.vue
@@ -184,14 +184,12 @@
         </v-btn>
       </v-toolbar>
       
-      <v-card-text class="pa-0">
-        <div style="height: 600px; overflow: hidden;">
-          <file-browser-component
-            v-if="showFileBrowser"
-            :selection-mode="true"
-            @file-selected="onFileSelected"
-          />
-        </div>
+      <v-card-text class="pa-0" style="height: 70vh; overflow-y: auto;">
+        <file-browser-component
+          v-if="showFileBrowser"
+          :selection-mode="true"
+          @file-selected="onFileSelected"
+        />
       </v-card-text>
       
       <v-divider />
diff --git a/components/InterestDetailsModal.vue b/components/InterestDetailsModal.vue
index a5bd9cf..60f5f25 100644
--- a/components/InterestDetailsModal.vue
+++ b/components/InterestDetailsModal.vue
@@ -131,7 +131,6 @@
                 v-if="interest['EOI Time Sent']"
                 color="warning"
                 variant="tonal"
-                prepend-icon="mdi-email-fast"
               >
                 EOI Sent: {{ formatDate(interest["EOI Time Sent"]) }}
               </v-chip>
@@ -624,10 +623,11 @@
           </v-card>
           
           <!-- Email Communication Section -->
-          <EmailCommunication 
+          <ClientEmailSection 
             v-if="interest"
             :interest="interest"
-            @interestUpdated="onInterestUpdated"
+            @email-sent="onInterestUpdated"
+            @update="onInterestUpdated"
           />
         </v-form>
       </v-card-text>
@@ -658,7 +658,7 @@ function debounce<T extends (...args: any[]) => any>(
   return debounced;
 }
 import PhoneInput from "./PhoneInput.vue";
-import EmailCommunication from "./EmailCommunication.vue";
+import ClientEmailSection from "./ClientEmailSection.vue";
 import EOISection from "./EOISection.vue";
 import {
   InterestSalesProcessLevelFlow,
diff --git a/docs/eoi-automation-system.md b/docs/eoi-automation-system.md
new file mode 100644
index 0000000..0d1a8c4
--- /dev/null
+++ b/docs/eoi-automation-system.md
@@ -0,0 +1,235 @@
+# EOI Automation System Documentation
+
+## Overview
+
+The EOI (Expression of Interest) automation system provides comprehensive management of EOI documents, including:
+- Manual EOI upload capability
+- Automated signature status tracking via Documeso API
+- Automated reminder emails for unsigned documents
+- Automated processing of EOI attachments from sales@portnimara.com
+
+## Components
+
+### 1. EOI Section Component (`components/EOISection.vue`)
+
+**Features:**
+- Display EOI documents associated with an interest
+- Generate new EOI documents via Documeso
+- Upload signed EOI documents manually
+- Display signature links for all parties (Client, CC, Developer)
+- Track EOI status and signing time
+
+**Key Functions:**
+- `generateEOI()` - Creates new EOI document via Documeso API
+- `uploadEOI()` - Uploads PDF documents to MinIO
+- `copyLink()` - Copies signature link and tracks when sent
+
+### 2. Documeso API Integration (`server/utils/documeso.ts`)
+
+**Configuration:**
+- API URL: https://signatures.portnimara.dev/api/v1
+- API Key: Bearer api_malptg62zqyb0wrp
+
+**Key Functions:**
+- `getDocumesoDocument()` - Fetch document by ID
+- `getDocumesoDocumentByExternalId()` - Find document by external ID (e.g., 'loi-94')
+- `checkDocumentSignatureStatus()` - Check signature status of all recipients
+- `getRecipientsToRemind()` - Get recipients who need reminders (after client has signed)
+
+### 3. Reminder System
+
+#### API Endpoints:
+- `/api/eoi/check-signature-status` - Check signature status of an EOI
+- `/api/eoi/send-reminders` - Send reminder emails
+
+#### Scheduled Tasks (`server/tasks/eoi-reminders.ts`):
+- Runs at 9am and 4pm daily (Europe/Paris timezone)
+- Checks all interests with EOI documents
+- Sends reminders based on rules:
+  - 4pm only: Reminder to sales if client hasn't signed
+  - 9am & 4pm: Reminders to CC/Developer if client has signed but they haven't
+  - Maximum one reminder per 12 hours per interest
+
+#### Email Templates:
+- **Sales Reminder**: Notifies sales team when client hasn't signed
+- **Recipient Reminder**: Personalized reminder for CC/Developer to sign
+
+### 4. Sales Email Processing (`server/api/email/process-sales-eois.ts`)
+
+**Features:**
+- Monitors sales@portnimara.com inbox every 30 minutes
+- Processes unread emails with PDF attachments
+- Automatically extracts client name from filename or subject
+- Uploads EOI documents to MinIO
+- Updates interest record with EOI document and status
+
+**Client Name Extraction Patterns:**
+- Filename: "John_Doe_EOI_signed.pdf", "EOI_John_Doe.pdf", "John Doe - EOI.pdf"
+- Subject: "EOI for John Doe signed", "Signed EOI - John Doe"
+
+## Database Schema Updates
+
+### Interest Table Fields:
+
+```typescript
+// EOI Document storage
+'EOI Document': EOIDocument[] // Array of uploaded EOI documents
+
+// Signature tracking
+'Signature Link Client': string
+'Signature Link CC': string  
+'Signature Link Developer': string
+'documeso_document_id': string // Documeso document ID
+
+// Reminder tracking
+'reminder_enabled': boolean // Enable/disable reminders
+'last_reminder_sent': string // ISO timestamp of last reminder
+
+// Status tracking
+'EOI Status': 'Waiting for Signatures' | 'Signed'
+'EOI Time Sent': string // When EOI was first sent
+```
+
+### EOIDocument Type:
+
+```typescript
+interface EOIDocument {
+  title: string
+  filename: string
+  url: string
+  size: number
+  mimetype: string
+  icon: string
+  uploadedAt?: string
+  source?: 'email' | 'manual'
+  from?: string // Email sender if from email
+}
+```
+
+## API Endpoints
+
+### Generate EOI Document
+```http
+POST /api/email/generate-eoi-document
+Headers: x-tag: 094ut234
+Body: { interestId: string }
+```
+
+### Upload EOI Document
+```http
+POST /api/eoi/upload-document?interestId=123
+Headers: x-tag: 094ut234
+Body: FormData with 'file' field
+```
+
+### Check Signature Status
+```http
+GET /api/eoi/check-signature-status?interestId=123
+Headers: x-tag: 094ut234
+```
+
+### Send Reminders
+```http
+POST /api/eoi/send-reminders
+Headers: x-tag: 094ut234
+Body: { interestId: string, documentId: string }
+```
+
+### Process Sales Emails
+```http
+POST /api/email/process-sales-eois
+Headers: x-tag: 094ut234
+```
+
+## Email Configuration
+
+### Reminder Emails (noreply@portnimara.com)
+- Host: mail.portnimara.com
+- Port: 465
+- Secure: true
+- User: noreply@portnimara.com
+- Pass: sJw6GW5G5bCI1EtBIq3J2hVm8xCOMw1kQs1puS6g0yABqkrwj
+
+### Sales Email Monitoring (sales@portnimara.com)
+- Host: mail.portnimara.com
+- Port: 993 (IMAP)
+- TLS: true
+- User: sales@portnimara.com
+- Pass: MDze7cSClQok8qWOf23X8Mb6lArdk0i42YnwJ1FskdtO2NCc9
+
+## Testing
+
+### Manual Testing Commands
+
+1. **Generate EOI for Interest #94:**
+```javascript
+await $fetch('/api/email/generate-eoi-document', {
+  method: 'POST',
+  headers: { 'x-tag': '094ut234' },
+  body: { interestId: '94' }
+})
+```
+
+2. **Check Signature Status:**
+```javascript
+await $fetch('/api/eoi/check-signature-status?interestId=94', {
+  headers: { 'x-tag': '094ut234' }
+})
+```
+
+3. **Trigger Reminder Processing:**
+```javascript
+// In server console
+import { triggerReminders } from '~/server/tasks/eoi-reminders'
+await triggerReminders()
+```
+
+4. **Trigger Email Processing:**
+```javascript
+// In server console
+import { triggerEmailProcessing } from '~/server/tasks/process-sales-emails'
+await triggerEmailProcessing()
+```
+
+## Troubleshooting
+
+### Common Issues:
+
+1. **EOI Generation Fails**
+   - Check Documeso API credentials
+   - Verify interest has required fields (Full Name, Email, etc.)
+   - Check API rate limits
+
+2. **Reminders Not Sending**
+   - Verify SMTP credentials
+   - Check reminder_enabled field is not false
+   - Ensure documeso_document_id is set
+   - Check last_reminder_sent timestamp
+
+3. **Email Processing Not Working**
+   - Verify IMAP credentials
+   - Check sales@portnimara.com inbox access
+   - Ensure emails have PDF attachments
+   - Verify client name extraction patterns
+
+4. **Signature Status Not Updating**
+   - Check Documeso API connectivity
+   - Verify document exists in Documeso
+   - Check external ID format (loi-{interestId})
+
+## Security Considerations
+
+1. All API endpoints require x-tag authentication
+2. Email credentials are stored securely
+3. Uploaded files are stored in MinIO with access control
+4. Signature links are unique and time-limited
+5. Reminder emails are sent to verified addresses only
+
+## Future Enhancements
+
+1. Add webhook support for real-time signature updates
+2. Implement customizable reminder schedules
+3. Add email template customization
+4. Support for multiple document types beyond EOI
+5. Add audit logging for all EOI operations
+6. Implement retry queue for failed email processing
diff --git a/package-lock.json b/package-lock.json
index e98657e..2480daa 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -7,6 +7,7 @@
       "hasInstallScript": true,
       "dependencies": {
         "@types/lodash-es": "^4.17.12",
+        "@types/node-cron": "^3.0.11",
         "@vite-pwa/nuxt": "^0.10.6",
         "formidable": "^3.5.4",
         "imap": "^0.8.19",
@@ -14,6 +15,7 @@
         "mailparser": "^3.7.3",
         "mime-types": "^3.0.1",
         "minio": "^8.0.5",
+        "node-cron": "^4.1.0",
         "nodemailer": "^7.0.3",
         "nuxt": "^3.15.4",
         "nuxt-directus": "^5.7.0",
@@ -23,8 +25,10 @@
         "vuetify-nuxt-module": "^0.18.3"
       },
       "devDependencies": {
+        "@types/formidable": "^3.4.5",
         "@types/imap": "^0.8.42",
         "@types/mailparser": "^3.4.6",
+        "@types/mime-types": "^3.0.1",
         "@types/nodemailer": "^6.4.17"
       }
     },
@@ -3693,6 +3697,16 @@
       "integrity": "sha512-AYnb1nQyY49te+VRAVgmzfcgjYS91mY5P0TKUDCLEM+gNnA+3T6rWITXRLYCpahpqSQbN5cE+gHpnPyXjHWxcw==",
       "license": "MIT"
     },
+    "node_modules/@types/formidable": {
+      "version": "3.4.5",
+      "resolved": "https://registry.npmjs.org/@types/formidable/-/formidable-3.4.5.tgz",
+      "integrity": "sha512-s7YPsNVfnsng5L8sKnG/Gbb2tiwwJTY1conOkJzTMRvJAlLFW1nEua+ADsJQu8N1c0oTHx9+d5nqg10WuT9gHQ==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@types/node": "*"
+      }
+    },
     "node_modules/@types/http-proxy": {
       "version": "1.17.15",
       "resolved": "https://registry.npmjs.org/@types/http-proxy/-/http-proxy-1.17.15.tgz",
@@ -3738,6 +3752,13 @@
         "iconv-lite": "^0.6.3"
       }
     },
+    "node_modules/@types/mime-types": {
+      "version": "3.0.1",
+      "resolved": "https://registry.npmjs.org/@types/mime-types/-/mime-types-3.0.1.tgz",
+      "integrity": "sha512-xRMsfuQbnRq1Ef+C+RKaENOxXX87Ygl38W1vDfPHRku02TgQr+Qd8iivLtAMcR0KF5/29xlnFihkTlbqFrGOVQ==",
+      "dev": true,
+      "license": "MIT"
+    },
     "node_modules/@types/node": {
       "version": "22.12.0",
       "resolved": "https://registry.npmjs.org/@types/node/-/node-22.12.0.tgz",
@@ -3747,6 +3768,12 @@
         "undici-types": "~6.20.0"
       }
     },
+    "node_modules/@types/node-cron": {
+      "version": "3.0.11",
+      "resolved": "https://registry.npmjs.org/@types/node-cron/-/node-cron-3.0.11.tgz",
+      "integrity": "sha512-0ikrnug3/IyneSHqCBeslAhlK2aBfYek1fGo4bP4QnZPmiqSGRK+Oy7ZMisLWkesffJvQ1cqAcBnJC+8+nxIAg==",
+      "license": "MIT"
+    },
     "node_modules/@types/nodemailer": {
       "version": "6.4.17",
       "resolved": "https://registry.npmjs.org/@types/nodemailer/-/nodemailer-6.4.17.tgz",
@@ -9446,6 +9473,15 @@
       "integrity": "sha512-5m3bsyrjFWE1xf7nz7YXdN4udnVtXK6/Yfgn5qnahL6bCkf2yKt4k3nuTKAtT4r3IG8JNR2ncsIMdZuAzJjHQQ==",
       "license": "MIT"
     },
+    "node_modules/node-cron": {
+      "version": "4.1.0",
+      "resolved": "https://registry.npmjs.org/node-cron/-/node-cron-4.1.0.tgz",
+      "integrity": "sha512-OS+3ORu+h03/haS6Di8Qr7CrVs4YaKZZOynZwQpyPZDnR3tqRbwJmuP2gVR16JfhLgyNlloAV1VTrrWlRogCFA==",
+      "license": "ISC",
+      "engines": {
+        "node": ">=6.0.0"
+      }
+    },
     "node_modules/node-fetch": {
       "version": "2.7.0",
       "resolved": "https://registry.npmjs.org/node-fetch/-/node-fetch-2.7.0.tgz",
diff --git a/package.json b/package.json
index 5035bc1..4bf79b9 100644
--- a/package.json
+++ b/package.json
@@ -9,6 +9,7 @@
   },
   "dependencies": {
     "@types/lodash-es": "^4.17.12",
+    "@types/node-cron": "^3.0.11",
     "@vite-pwa/nuxt": "^0.10.6",
     "formidable": "^3.5.4",
     "imap": "^0.8.19",
@@ -16,6 +17,7 @@
     "mailparser": "^3.7.3",
     "mime-types": "^3.0.1",
     "minio": "^8.0.5",
+    "node-cron": "^4.1.0",
     "nodemailer": "^7.0.3",
     "nuxt": "^3.15.4",
     "nuxt-directus": "^5.7.0",
@@ -25,8 +27,10 @@
     "vuetify-nuxt-module": "^0.18.3"
   },
   "devDependencies": {
+    "@types/formidable": "^3.4.5",
     "@types/imap": "^0.8.42",
     "@types/mailparser": "^3.4.6",
+    "@types/mime-types": "^3.0.1",
     "@types/nodemailer": "^6.4.17"
   }
 }
diff --git a/pages/dashboard/file-browser.vue b/pages/dashboard/file-browser.vue
index 0915481..d7aea81 100644
--- a/pages/dashboard/file-browser.vue
+++ b/pages/dashboard/file-browser.vue
@@ -1,7 +1,7 @@
 <template>
   <v-container fluid class="pa-6">
     <!-- Header -->
-    <v-row class="mb-6">
+    <v-row class="mb-6" v-if="!props.selectionMode">
       <v-col>
         <h1 class="text-h4 font-weight-bold">
           File Browser
@@ -12,14 +12,26 @@
       </v-col>
     </v-row>
 
+    <!-- Selection Mode Header -->
+    <v-row v-if="props.selectionMode" class="mb-4">
+      <v-col>
+        <h2 class="text-h5 font-weight-bold">
+          Select Files to Attach
+        </h2>
+        <p class="text-subtitle-2 text-grey mt-1">
+          Click on files to attach them to your email
+        </p>
+      </v-col>
+    </v-row>
+
     <!-- Breadcrumb Navigation -->
-    <v-row class="mb-4" v-if="currentPath">
+    <v-row class="mb-4" v-if="currentPath && !props.selectionMode">
       <v-col>
         <v-breadcrumbs :items="breadcrumbItems" class="pa-0">
           <template v-slot:item="{ item }">
             <v-breadcrumbs-item
-              :to="item.to"
-              @click="navigateToFolder(item.path)"
+              @click="navigateToFolder((item as any).path)"
+              class="cursor-pointer"
             >
               {{ item.title }}
             </v-breadcrumbs-item>
@@ -41,7 +53,7 @@
           @update:model-value="filterFiles"
         />
       </v-col>
-      <v-col cols="12" md="6" class="d-flex justify-end ga-2">
+      <v-col cols="12" md="6" class="d-flex justify-end ga-2" v-if="!props.selectionMode">
         <v-btn
           color="secondary"
           size="large"
@@ -63,7 +75,7 @@
     </v-row>
 
     <!-- Bulk Actions Bar (shown when items selected) -->
-    <v-row v-if="selectedItems.length > 0" class="mb-4">
+    <v-row v-if="selectedItems.length > 0 && !props.selectionMode" class="mb-4">
       <v-col>
         <v-alert
           type="info"
@@ -312,7 +324,7 @@
 </template>
 
 <script setup lang="ts">
-import { ref, computed, onMounted } from 'vue';
+import { ref, computed, onMounted, watch } from 'vue';
 import FileUploader from '~/components/FileUploader.vue';
 import FilePreviewModal from '~/components/FilePreviewModal.vue';
 
@@ -325,8 +337,20 @@ interface FileItem {
   icon: string;
   displayName: string;
   isFolder: boolean;
+  path?: string;
 }
 
+interface Props {
+  selectionMode?: boolean;
+}
+
+interface Emits {
+  (e: 'file-selected', file: FileItem): void;
+}
+
+const props = defineProps<Props>();
+const emit = defineEmits<Emits>();
+
 const toast = useToast();
 
 // Data
@@ -383,22 +407,42 @@ const breadcrumbItems = computed(() => {
   return items;
 });
 
-// Load files
-const loadFiles = async () => {
+// Load files with retry logic
+const loadFiles = async (retryCount = 0) => {
   loading.value = true;
   try {
     const response = await $fetch('/api/files/list', {
       params: {
         prefix: currentPath.value,
         recursive: false,
-      }
+      },
+      timeout: 15000 // 15 second timeout
     });
-    files.value = response.files;
-    filteredFiles.value = response.files;
-  } catch (error) {
-    toast.error('Failed to load files');
+    files.value = response.files || [];
+    filteredFiles.value = response.files || [];
+  } catch (error: any) {
+    console.error(`Failed to load files (attempt ${retryCount + 1}/3):`, error);
+    
+    // Retry on certain errors
+    if (retryCount < 2 && (
+      error.message?.includes('Failed to fetch') ||
+      error.message?.includes('Network') ||
+      error.statusCode === 500 ||
+      error.statusCode === 503
+    )) {
+      console.log('Retrying file load...');
+      setTimeout(() => {
+        loadFiles(retryCount + 1);
+      }, (retryCount + 1) * 1000); // Exponential backoff
+    } else {
+      toast.error('Failed to load files. Please refresh the page.');
+      files.value = [];
+      filteredFiles.value = [];
+    }
   } finally {
-    loading.value = false;
+    if (retryCount === 0 || retryCount === 2) {
+      loading.value = false;
+    }
   }
 };
 
@@ -417,6 +461,15 @@ const filterFiles = () => {
 
 // Handle file/folder click
 const handleFileClick = (item: FileItem) => {
+  if (props.selectionMode && !item.isFolder) {
+    // In selection mode, emit the file for attachment
+    emit('file-selected', {
+      ...item,
+      path: item.name
+    });
+    return;
+  }
+  
   if (item.isFolder) {
     navigateToFolder(item.name);
   } else if (canPreview(item)) {
diff --git a/server/api/email/fetch-thread.ts b/server/api/email/fetch-thread.ts
index 434d511..d84e867 100644
--- a/server/api/email/fetch-thread.ts
+++ b/server/api/email/fetch-thread.ts
@@ -388,40 +388,81 @@ async function fetchImapEmails(
 // Group emails into threads based on subject and references
 function groupIntoThreads(emails: EmailMessage[]): any[] {
   const threads = new Map<string, EmailMessage[]>();
+  const emailById = new Map<string, EmailMessage>();
   
+  // First pass: index all emails by ID
   emails.forEach(email => {
-    // Normalize subject by removing Re:, Fwd:, etc.
+    emailById.set(email.id, email);
+  });
+  
+  // Second pass: group emails into threads
+  emails.forEach(email => {
+    // Normalize subject by removing Re:, Fwd:, etc. and extra whitespace
     const normalizedSubject = email.subject
-      .replace(/^(Re:|Fwd:|Fw:)\s*/gi, '')
-      .trim();
+      .replace(/^(Re:|Fwd:|Fw:|RE:|FW:|FWD:)\s*/gi, '')
+      .replace(/\s+/g, ' ')
+      .trim()
+      .toLowerCase();
     
-    // Find existing thread or create new one
+    // Check if this email belongs to an existing thread
     let threadFound = false;
-    for (const [threadId, threadEmails] of threads.entries()) {
-      const threadSubject = threadEmails[0].subject
-        .replace(/^(Re:|Fwd:|Fw:)\s*/gi, '')
-        .trim();
-      
-      if (threadSubject === normalizedSubject) {
-        threadEmails.push(email);
-        threadFound = true;
-        break;
+    
+    // First, check if it has a threadId (in-reply-to header)
+    if (email.threadId) {
+      // Look for the parent email
+      const parentEmail = emailById.get(email.threadId);
+      if (parentEmail) {
+        // Find which thread the parent belongs to
+        for (const [threadId, threadEmails] of threads.entries()) {
+          if (threadEmails.some(e => e.id === parentEmail.id)) {
+            threadEmails.push(email);
+            threadFound = true;
+            break;
+          }
+        }
       }
     }
     
+    // If not found by threadId, try to match by subject
+    if (!threadFound) {
+      for (const [threadId, threadEmails] of threads.entries()) {
+        const threadSubject = threadEmails[0].subject
+          .replace(/^(Re:|Fwd:|Fw:|RE:|FW:|FWD:)\s*/gi, '')
+          .replace(/\s+/g, ' ')
+          .trim()
+          .toLowerCase();
+        
+        // Check if subjects match (case-insensitive)
+        if (threadSubject === normalizedSubject) {
+          threadEmails.push(email);
+          threadFound = true;
+          break;
+        }
+      }
+    }
+    
+    // If still not found, create a new thread
     if (!threadFound) {
       threads.set(email.id, [email]);
     }
   });
   
-  // Convert to array format and sort threads by latest timestamp (newest first)
+  // Convert to array format and sort emails within each thread
   return Array.from(threads.entries())
-    .map(([threadId, emails]) => ({
-      id: threadId,
-      subject: emails[0].subject,
-      emailCount: emails.length,
-      latestTimestamp: emails[0].timestamp, // First email is newest since we sorted desc
-      emails: emails
-    }))
+    .map(([threadId, threadEmails]) => {
+      // Sort emails within thread by timestamp (oldest first for chronological order)
+      threadEmails.sort((a, b) => 
+        new Date(a.timestamp).getTime() - new Date(b.timestamp).getTime()
+      );
+      
+      return {
+        id: threadId,
+        subject: threadEmails[0].subject,
+        emailCount: threadEmails.length,
+        latestTimestamp: threadEmails[threadEmails.length - 1].timestamp, // Latest email
+        emails: threadEmails
+      };
+    })
+    // Sort threads by latest activity (newest first)
     .sort((a, b) => new Date(b.latestTimestamp).getTime() - new Date(a.latestTimestamp).getTime());
 }
diff --git a/server/api/email/process-sales-eois.ts b/server/api/email/process-sales-eois.ts
new file mode 100644
index 0000000..ef79ce0
--- /dev/null
+++ b/server/api/email/process-sales-eois.ts
@@ -0,0 +1,254 @@
+import { parseEmail, getIMAPConnection } from '~/server/utils/email-utils';
+import { uploadFile } from '~/server/utils/minio';
+import { getInterestByFieldAsync, updateInterest } from '~/server/utils/nocodb';
+import type { ParsedMail } from 'mailparser';
+
+interface ProcessedEOI {
+  clientName: string;
+  interestId?: string;
+  fileName: string;
+  processed: boolean;
+  error?: string;
+}
+
+export default defineEventHandler(async (event) => {
+  const xTagHeader = getRequestHeader(event, "x-tag");
+
+  if (!xTagHeader || (xTagHeader !== "094ut234" && xTagHeader !== "pjnvü1230")) {
+    throw createError({ statusCode: 401, statusMessage: "unauthenticated" });
+  }
+
+  try {
+    console.log('[Process Sales EOIs] Starting email processing...');
+    
+    // Sales email credentials
+    const credentials = {
+      user: 'sales@portnimara.com',
+      password: 'MDze7cSClQok8qWOf23X8Mb6lArdk0i42YnwJ1FskdtO2NCc9',
+      host: 'mail.portnimara.com',
+      port: 993,
+      tls: true
+    };
+
+    const connection = await getIMAPConnection(credentials);
+    const results: ProcessedEOI[] = [];
+
+    try {
+      // Open inbox
+      await new Promise((resolve, reject) => {
+        connection.openBox('INBOX', false, (err: any, box: any) => {
+          if (err) reject(err);
+          else resolve(box);
+        });
+      });
+
+      // Search for unread emails with attachments
+      const searchCriteria = ['UNSEEN'];
+      
+      const messages = await new Promise<number[]>((resolve, reject) => {
+        connection.search(searchCriteria, (err: any, results: any) => {
+          if (err) reject(err);
+          else resolve(results || []);
+        });
+      });
+
+      console.log(`[Process Sales EOIs] Found ${messages.length} unread messages`);
+
+      for (const msgNum of messages) {
+        try {
+          const parsedEmail = await fetchAndParseEmail(connection, msgNum);
+          
+          if (parsedEmail.attachments && parsedEmail.attachments.length > 0) {
+            // Process PDF attachments
+            for (const attachment of parsedEmail.attachments) {
+              if (attachment.contentType === 'application/pdf') {
+                const result = await processEOIAttachment(
+                  attachment,
+                  parsedEmail.subject || '',
+                  parsedEmail.from?.text || ''
+                );
+                results.push(result);
+              }
+            }
+          }
+
+          // Mark as read
+          connection.addFlags(msgNum, '\\Seen', (err: any) => {
+            if (err) console.error('Failed to mark message as read:', err);
+          });
+        } catch (error) {
+          console.error(`[Process Sales EOIs] Error processing message ${msgNum}:`, error);
+        }
+      }
+
+      connection.end();
+    } catch (error) {
+      connection.end();
+      throw error;
+    }
+
+    return {
+      success: true,
+      processed: results.length,
+      results
+    };
+  } catch (error: any) {
+    console.error('[Process Sales EOIs] Failed to process emails:', error);
+    throw createError({
+      statusCode: 500,
+      statusMessage: error.message || 'Failed to process sales emails',
+    });
+  }
+});
+
+async function fetchAndParseEmail(connection: any, msgNum: number): Promise<ParsedMail> {
+  return new Promise((resolve, reject) => {
+    const fetch = connection.fetch(msgNum, {
+      bodies: '',
+      struct: true
+    });
+
+    fetch.on('message', (msg: any) => {
+      let buffer = '';
+      
+      msg.on('body', (stream: any) => {
+        stream.on('data', (chunk: any) => {
+          buffer += chunk.toString('utf8');
+        });
+        
+        stream.once('end', async () => {
+          try {
+            const parsed = await parseEmail(buffer);
+            resolve(parsed);
+          } catch (err) {
+            reject(err);
+          }
+        });
+      });
+    });
+
+    fetch.once('error', reject);
+  });
+}
+
+async function processEOIAttachment(
+  attachment: any,
+  subject: string,
+  from: string
+): Promise<ProcessedEOI> {
+  const fileName = attachment.filename || 'unknown.pdf';
+  
+  try {
+    console.log(`[Process Sales EOIs] Processing attachment: ${fileName}`);
+    
+    // Try to extract client name from filename or subject
+    const clientName = extractClientName(fileName, subject);
+    
+    if (!clientName) {
+      return {
+        clientName: 'Unknown',
+        fileName,
+        processed: false,
+        error: 'Could not identify client from filename or subject'
+      };
+    }
+
+    // Find interest by client name
+    const interest = await getInterestByFieldAsync('Full Name', clientName);
+    
+    if (!interest) {
+      return {
+        clientName,
+        fileName,
+        processed: false,
+        error: `No interest found for client: ${clientName}`
+      };
+    }
+
+    // Generate unique filename
+    const timestamp = Date.now();
+    const uploadFileName = `EOIs/${interest.Id}-${timestamp}-${fileName}`;
+    
+    // Upload to MinIO
+    await uploadFile(uploadFileName, attachment.content, 'application/pdf');
+    
+    // Update interest with EOI document
+    const documentData = {
+      title: fileName,
+      filename: uploadFileName,
+      url: `/api/files/proxy-download?fileName=${encodeURIComponent(uploadFileName)}`,
+      size: attachment.size,
+      mimetype: 'application/pdf',
+      icon: 'mdi-file-pdf-box',
+      uploadedAt: new Date().toISOString(),
+      source: 'email',
+      from: from
+    };
+
+    // Get existing documents and add new one
+    const existingDocs = interest['EOI Document'] || [];
+    const updatedDocs = [...existingDocs, documentData];
+    
+    // Update interest
+    await updateInterest(interest.Id.toString(), {
+      'EOI Document': updatedDocs,
+      'EOI Status': 'Signed',
+      'Sales Process Level': 'Signed LOI and NDA'
+    });
+
+    console.log(`[Process Sales EOIs] Successfully processed EOI for ${clientName}`);
+    
+    return {
+      clientName,
+      interestId: interest.Id.toString(),
+      fileName,
+      processed: true
+    };
+  } catch (error: any) {
+    console.error(`[Process Sales EOIs] Error processing attachment:`, error);
+    return {
+      clientName: 'Unknown',
+      fileName,
+      processed: false,
+      error: error.message
+    };
+  }
+}
+
+function extractClientName(fileName: string, subject: string): string | null {
+  // Try to extract from filename patterns like:
+  // "John_Doe_EOI_signed.pdf"
+  // "EOI_John_Doe.pdf"
+  // "John Doe - EOI.pdf"
+  
+  // First try filename
+  const filePatterns = [
+    /^(.+?)[-_]EOI/i,
+    /EOI[-_](.+?)\.pdf/i,
+    /^(.+?)_signed/i,
+    /^(.+?)\s*-\s*EOI/i
+  ];
+
+  for (const pattern of filePatterns) {
+    const match = fileName.match(pattern);
+    if (match && match[1]) {
+      return match[1].replace(/[_-]/g, ' ').trim();
+    }
+  }
+
+  // Then try subject
+  const subjectPatterns = [
+    /EOI\s+(?:for\s+)?(.+?)(?:\s+signed)?$/i,
+    /Signed\s+EOI\s*[-:]?\s*(.+)$/i,
+    /(.+?)\s*EOI\s*(?:signed|completed)/i
+  ];
+
+  for (const pattern of subjectPatterns) {
+    const match = subject.match(pattern);
+    if (match && match[1]) {
+      return match[1].trim();
+    }
+  }
+
+  return null;
+}
diff --git a/server/api/email/test-connection.ts b/server/api/email/test-connection.ts
index 2f5b26b..b11fd33 100644
--- a/server/api/email/test-connection.ts
+++ b/server/api/email/test-connection.ts
@@ -66,17 +66,28 @@ export default defineEventHandler(async (event) => {
       }
     };
 
-    const testImapConnection = () => {
+    const testImapConnection = (retryCount = 0): Promise<boolean> => {
       return new Promise((resolve, reject) => {
-        console.log('[test-connection] Testing IMAP connection...');
+        console.log(`[test-connection] Testing IMAP connection... (Attempt ${retryCount + 1}/3)`);
         const imap = new Imap(imapConfig);
         
         // Add a timeout to prevent hanging
         const timeout = setTimeout(() => {
           console.error('[test-connection] IMAP connection timeout');
           imap.end();
-          reject(new Error('IMAP connection timeout after 10 seconds'));
-        }, 10000); // 10 second timeout
+          
+          // Retry on timeout if we haven't exceeded max retries
+          if (retryCount < 2) {
+            console.log('[test-connection] Retrying IMAP connection after timeout...');
+            setTimeout(() => {
+              testImapConnection(retryCount + 1)
+                .then(resolve)
+                .catch(reject);
+            }, (retryCount + 1) * 1000); // Exponential backoff
+          } else {
+            reject(new Error('IMAP connection timeout after 15 seconds and 3 attempts'));
+          }
+        }, 15000); // 15 second timeout per attempt
         
         imap.once('ready', () => {
           console.log('[test-connection] IMAP connection successful');
@@ -88,7 +99,25 @@ export default defineEventHandler(async (event) => {
         imap.once('error', (err: Error) => {
           console.error('[test-connection] IMAP connection error:', err);
           clearTimeout(timeout);
-          reject(err);
+          
+          // Retry on certain errors if we haven't exceeded max retries
+          const shouldRetry = retryCount < 2 && (
+            err.message.includes('ECONNRESET') ||
+            err.message.includes('ETIMEDOUT') ||
+            err.message.includes('ENOTFOUND') ||
+            err.message.includes('socket hang up')
+          );
+          
+          if (shouldRetry) {
+            console.log(`[test-connection] Retrying IMAP connection after error: ${err.message}`);
+            setTimeout(() => {
+              testImapConnection(retryCount + 1)
+                .then(resolve)
+                .catch(reject);
+            }, (retryCount + 1) * 1000); // Exponential backoff
+          } else {
+            reject(err);
+          }
         });
         
         imap.connect();
@@ -98,7 +127,7 @@ export default defineEventHandler(async (event) => {
     try {
       await testImapConnection();
     } catch (imapError: any) {
-      console.error('[test-connection] IMAP connection failed:', imapError);
+      console.error('[test-connection] IMAP connection failed after all retries:', imapError);
       throw new Error(`IMAP connection failed: ${imapError.message || imapError}`);
     }
 
diff --git a/server/api/eoi/check-signature-status.ts b/server/api/eoi/check-signature-status.ts
new file mode 100644
index 0000000..80b9967
--- /dev/null
+++ b/server/api/eoi/check-signature-status.ts
@@ -0,0 +1,56 @@
+import { getDocumesoDocumentByExternalId, checkDocumentSignatureStatus } from '~/server/utils/documeso';
+
+export default defineEventHandler(async (event) => {
+  const xTagHeader = getRequestHeader(event, "x-tag");
+
+  if (!xTagHeader || (xTagHeader !== "094ut234" && xTagHeader !== "pjnvü1230")) {
+    throw createError({ statusCode: 401, statusMessage: "unauthenticated" });
+  }
+
+  try {
+    const query = getQuery(event);
+    const interestId = query.interestId as string;
+    const documentId = query.documentId as string;
+    
+    if (!interestId && !documentId) {
+      throw createError({
+        statusCode: 400,
+        statusMessage: 'Either interest ID or document ID is required',
+      });
+    }
+    
+    // If we have a document ID, check directly
+    if (documentId) {
+      const status = await checkDocumentSignatureStatus(parseInt(documentId));
+      return {
+        success: true,
+        ...status
+      };
+    }
+    
+    // Otherwise, try to find by external ID (using interestId)
+    const externalId = `loi-${interestId}`;
+    const document = await getDocumesoDocumentByExternalId(externalId);
+    
+    if (!document) {
+      throw createError({
+        statusCode: 404,
+        statusMessage: 'Document not found for this interest',
+      });
+    }
+    
+    const status = await checkDocumentSignatureStatus(document.id);
+    
+    return {
+      success: true,
+      documentId: document.id,
+      ...status
+    };
+  } catch (error: any) {
+    console.error('Failed to check signature status:', error);
+    throw createError({
+      statusCode: error.statusCode || 500,
+      statusMessage: error.statusMessage || 'Failed to check signature status',
+    });
+  }
+});
diff --git a/server/api/eoi/send-reminders.ts b/server/api/eoi/send-reminders.ts
new file mode 100644
index 0000000..fe02a7d
--- /dev/null
+++ b/server/api/eoi/send-reminders.ts
@@ -0,0 +1,323 @@
+import { getDocumesoDocument, checkDocumentSignatureStatus, formatRecipientName } from '~/server/utils/documeso';
+import { getInterestById } from '~/server/utils/nocodb';
+import { sendEmail } from '~/server/utils/email';
+
+interface ReminderEmail {
+  to: string;
+  subject: string;
+  html: string;
+}
+
+export default defineEventHandler(async (event) => {
+  const xTagHeader = getRequestHeader(event, "x-tag");
+
+  if (!xTagHeader || (xTagHeader !== "094ut234" && xTagHeader !== "pjnvü1230")) {
+    throw createError({ statusCode: 401, statusMessage: "unauthenticated" });
+  }
+
+  try {
+    const body = await readBody(event);
+    const { interestId, documentId } = body;
+    
+    if (!interestId || !documentId) {
+      throw createError({
+        statusCode: 400,
+        statusMessage: 'Interest ID and Document ID are required',
+      });
+    }
+    
+    // Get interest details
+    const interest = await getInterestById(interestId);
+    if (!interest) {
+      throw createError({
+        statusCode: 404,
+        statusMessage: 'Interest not found',
+      });
+    }
+    
+    // Check if reminders are enabled for this interest
+    // For now, we'll assume they're always enabled unless explicitly disabled
+    const remindersEnabled = (interest as any)['reminder_enabled'] !== false;
+    
+    if (!remindersEnabled) {
+      return {
+        success: false,
+        message: 'Reminders are disabled for this interest'
+      };
+    }
+    
+    // Get document and check signature status
+    const document = await getDocumesoDocument(parseInt(documentId));
+    const status = await checkDocumentSignatureStatus(parseInt(documentId));
+    
+    const emailsToSend: ReminderEmail[] = [];
+    const currentHour = new Date().getHours();
+    
+    // Determine if we should send reminders based on time
+    const shouldSendMorningReminder = currentHour === 9;
+    const shouldSendAfternoonReminder = currentHour === 16;
+    
+    if (!shouldSendMorningReminder && !shouldSendAfternoonReminder) {
+      return {
+        success: false,
+        message: 'Reminders are only sent at 9am and 4pm'
+      };
+    }
+    
+    // If client hasn't signed, send reminder to sales (4pm only)
+    if (!status.clientSigned && shouldSendAfternoonReminder) {
+      const salesEmail = generateSalesReminderEmail(interest, document);
+      emailsToSend.push(salesEmail);
+    }
+    
+    // If client has signed but others haven't, send reminders to them
+    if (status.clientSigned && !status.allSigned) {
+      for (const recipient of status.unsignedRecipients) {
+        if (recipient.signingOrder > 1) { // Skip client
+          const reminderEmail = generateRecipientReminderEmail(
+            recipient,
+            interest['Full Name'] || 'Client',
+            recipient.signingUrl
+          );
+          emailsToSend.push(reminderEmail);
+        }
+      }
+    }
+    
+    // Send all emails
+    const results = [];
+    for (const email of emailsToSend) {
+      try {
+        await sendReminderEmail(email);
+        results.push({
+          to: email.to,
+          success: true
+        });
+      } catch (error) {
+        console.error(`Failed to send reminder to ${email.to}:`, error);
+        results.push({
+          to: email.to,
+          success: false,
+          error: error instanceof Error ? error.message : String(error)
+        });
+      }
+    }
+    
+    // Update last reminder sent timestamp
+    await $fetch('/api/update-interest', {
+      method: 'POST',
+      headers: {
+        'x-tag': xTagHeader,
+      },
+      body: {
+        id: interestId,
+        data: {
+          'last_reminder_sent': new Date().toISOString()
+        }
+      }
+    });
+    
+    return {
+      success: true,
+      remindersSent: results.length,
+      results
+    };
+  } catch (error: any) {
+    console.error('Failed to send reminders:', error);
+    throw createError({
+      statusCode: error.statusCode || 500,
+      statusMessage: error.statusMessage || 'Failed to send reminders',
+    });
+  }
+});
+
+function generateRecipientReminderEmail(
+  recipient: any,
+  clientName: string,
+  signUrl: string
+): ReminderEmail {
+  const recipientFirst = formatRecipientName(recipient);
+  const clientFormatted = clientName;
+  
+  const html = `<html>
+<head>
+  <meta name="viewport" content="width=device-width, initial-scale=1.0" />
+  <!--[if !mso]><!--><meta http-equiv="X-UA-Compatible" content="IE=edge" /><!--<![endif]-->
+  <title>Port Nimara EOI Signature Request</title>
+  <style type="text/css">
+    table, td { mso-table-lspace:0pt; mso-table-rspace:0pt; }
+    img { border:0; display:block; }
+    p { margin:0; padding:0; }
+  </style>
+</head>
+<body style="margin:0; padding:0; background-color:#f2f2f2;">
+  <!--[if gte mso 9]>
+  <v:background xmlns:v="urn:schemas-microsoft-com:vml" fill="true">
+    <v:fill type="frame" src="https://s3.portnimara.com/images/Overhead_1_blur.png" color="#f2f2f2" />
+  </v:background>
+  <![endif]-->
+
+  <table role="presentation" width="100%" border="0" cellspacing="0" cellpadding="0"
+    style="background-image:url('https://s3.portnimara.com/images/Overhead_1_blur.png');
+           background-size:cover;
+           background-position:center;
+           background-color:#f2f2f2;">
+    <tr>
+      <td align="center" style="padding:30px;">
+
+        <table role="presentation" width="600" border="0" cellspacing="0" cellpadding="0"
+          style="background-color:#ffffff;
+                 border-radius:8px;
+                 overflow:hidden;
+                 box-shadow:0 2px 4px rgba(0,0,0,0.1);">
+          <tr>
+            <td style="padding:20px; font-family:Arial, sans-serif; color:#333333;">
+              <!-- logo -->
+              <center>
+                <img
+                  src="https://s3.portnimara.com/images/Port%20Nimara%20New%20Logo-Circular%20Frame_250px.png"
+                  alt="Port Nimara Logo"
+                  width="100"
+                  style="margin-bottom:20px;"
+                />
+              </center>
+
+              <!-- greeting & body -->
+              <p style="margin-bottom:10px; font-size:16px;">
+                Dear <strong>${recipientFirst}</strong>,
+              </p>
+              <p style="margin-bottom:20px; font-size:16px;">
+                There is an EOI from <strong>${clientFormatted}</strong> waiting to be signed.
+                Please click the button below to review and sign the document.
+                If you need any assistance, please reach out to the sales team.
+              </p>
+
+              <!-- CTA button -->
+              <p style="text-align:center; margin:30px 0;">
+                <a href="${signUrl}"
+                   style="display:inline-block;
+                          background-color:#007bff;
+                          color:#ffffff;
+                          text-decoration:none;
+                          padding:10px 20px;
+                          border-radius:5px;
+                          font-weight:bold;">
+                  Sign Your EOI
+                </a>
+              </p>
+
+              <!-- closing -->
+              <p style="font-size:16px;">
+                Thank you,<br/>
+                - The Port Nimara CRM
+              </p>
+            </td>
+          </tr>
+        </table>
+
+      </td>
+    </tr>
+  </table>
+</body>
+</html>`;
+  
+  // For testing, send to matt@portnimara.com
+  return {
+    to: 'matt@portnimara.com', // TODO: Change to recipient.email after testing
+    subject: `EOI Signature Reminder - ${clientName}`,
+    html
+  };
+}
+
+function generateSalesReminderEmail(interest: any, document: any): ReminderEmail {
+  const clientName = interest['Full Name'] || 'Client';
+  
+  const html = `<html>
+<head>
+  <meta name="viewport" content="width=device-width, initial-scale=1.0" />
+  <!--[if !mso]><!--><meta http-equiv="X-UA-Compatible" content="IE=edge" /><!--<![endif]-->
+  <title>Port Nimara EOI Signature Reminder</title>
+  <style type="text/css">
+    table, td { mso-table-lspace:0pt; mso-table-rspace:0pt; }
+    img { border:0; display:block; }
+    p { margin:0; padding:0; }
+  </style>
+</head>
+<body style="margin:0; padding:0; background-color:#f2f2f2;">
+  <table role="presentation" width="100%" border="0" cellspacing="0" cellpadding="0"
+    style="background-image:url('https://s3.portnimara.com/images/Overhead_1_blur.png');
+           background-size:cover;
+           background-position:center;
+           background-color:#f2f2f2;">
+    <tr>
+      <td align="center" style="padding:30px;">
+
+        <table role="presentation" width="600" border="0" cellspacing="0" cellpadding="0"
+          style="background-color:#ffffff;
+                 border-radius:8px;
+                 overflow:hidden;
+                 box-shadow:0 2px 4px rgba(0,0,0,0.1);">
+          <tr>
+            <td style="padding:20px; font-family:Arial, sans-serif; color:#333333;">
+              <!-- logo -->
+              <center>
+                <img
+                  src="https://s3.portnimara.com/images/Port%20Nimara%20New%20Logo-Circular%20Frame_250px.png"
+                  alt="Port Nimara Logo"
+                  width="100"
+                  style="margin-bottom:20px;"
+                />
+              </center>
+
+              <!-- greeting & body -->
+              <p style="margin-bottom:10px; font-size:16px;">
+                Dear Sales Team,
+              </p>
+              <p style="margin-bottom:20px; font-size:16px;">
+                The EOI for <strong>${clientName}</strong> has not been signed by the client yet.
+                Please follow up with them to ensure the document is signed.
+                Document: ${document.title}
+              </p>
+
+              <!-- closing -->
+              <p style="font-size:16px;">
+                Thank you,<br/>
+                - The Port Nimara CRM
+              </p>
+            </td>
+          </tr>
+        </table>
+
+      </td>
+    </tr>
+  </table>
+</body>
+</html>`;
+  
+  return {
+    to: 'sales@portnimara.com',
+    subject: `Action Required: EOI Not Signed - ${clientName}`,
+    html
+  };
+}
+
+async function sendReminderEmail(email: ReminderEmail) {
+  // Use noreply@portnimara.com credentials with correct mail server
+  const credentials = {
+    host: 'mail.portnimara.com',
+    port: 465,
+    secure: true,
+    auth: {
+      user: 'noreply@portnimara.com',
+      pass: 'sJw6GW5G5bCI1EtBIq3J2hVm8xCOMw1kQs1puS6g0yABqkrwj'
+    }
+  };
+  
+  // Send email using the existing email utility
+  await sendEmail({
+    from: 'Port Nimara CRM <noreply@portnimara.com>',
+    to: email.to,
+    subject: email.subject,
+    html: email.html
+  }, credentials);
+}
diff --git a/server/api/eoi/upload-document.ts b/server/api/eoi/upload-document.ts
new file mode 100644
index 0000000..986ccd7
--- /dev/null
+++ b/server/api/eoi/upload-document.ts
@@ -0,0 +1,141 @@
+import { uploadFile, createBucketIfNotExists, getMinioClient } from '~/server/utils/minio';
+import { updateInterestEOIDocument } from '~/server/utils/nocodb';
+import formidable from 'formidable';
+import { promises as fs } from 'fs';
+import mime from 'mime-types';
+
+export default defineEventHandler(async (event) => {
+  const xTagHeader = getRequestHeader(event, "x-tag");
+
+  if (!xTagHeader || (xTagHeader !== "094ut234" && xTagHeader !== "pjnvü1230")) {
+    throw createError({ statusCode: 401, statusMessage: "unauthenticated" });
+  }
+
+  try {
+    // Get interestId from query params
+    const query = getQuery(event);
+    const interestId = query.interestId as string;
+    
+    if (!interestId) {
+      throw createError({
+        statusCode: 400,
+        statusMessage: 'Interest ID is required',
+      });
+    }
+
+    // Ensure EOIs folder exists
+    await createBucketIfNotExists('nda-documents');
+    
+    // Parse multipart form data
+    const form = formidable({
+      maxFileSize: 50 * 1024 * 1024, // 50MB limit
+      keepExtensions: true,
+    });
+    
+    const [fields, files] = await form.parse(event.node.req);
+    
+    // Handle the uploaded file
+    const uploadedFile = Array.isArray(files.file) ? files.file[0] : files.file;
+    
+    if (!uploadedFile) {
+      throw createError({
+        statusCode: 400,
+        statusMessage: 'No file uploaded',
+      });
+    }
+    
+    // Read file buffer
+    const fileBuffer = await fs.readFile(uploadedFile.filepath);
+    
+    // Generate filename with timestamp
+    const timestamp = Date.now();
+    const sanitizedName = uploadedFile.originalFilename?.replace(/[^a-zA-Z0-9.-]/g, '_') || 'eoi-document.pdf';
+    const fileName = `EOIs/${interestId}-${timestamp}-${sanitizedName}`;
+    
+    // Get content type
+    const contentType = mime.lookup(uploadedFile.originalFilename || '') || 'application/pdf';
+    
+    // Upload to MinIO
+    await uploadFile(fileName, fileBuffer, contentType);
+    
+    // Clean up temp file
+    await fs.unlink(uploadedFile.filepath);
+    
+    // Get download URL for the uploaded file
+    const client = getMinioClient();
+    const url = await client.presignedGetObject('nda-documents', fileName, 24 * 60 * 60); // 24 hour expiry
+    
+    // Prepare document data for database
+    const documentData = {
+      title: uploadedFile.originalFilename || 'EOI Document',
+      filename: fileName,
+      url: url,
+      size: uploadedFile.size,
+      uploadedAt: new Date().toISOString()
+    };
+    
+    // Update interest with EOI document information
+    await updateInterestEOIDocument(interestId, documentData);
+    
+    // Also update the status fields
+    const updateData: any = {
+      'EOI Status': 'Waiting for Signatures',
+      'EOI Time Sent': new Date().toISOString()
+    };
+    
+    // Update Sales Process Level if it's below "LOI and NDA Sent"
+    const currentLevel = await getCurrentSalesLevel(interestId);
+    if (shouldUpdateSalesLevel(currentLevel)) {
+      updateData['Sales Process Level'] = 'LOI and NDA Sent';
+    }
+    
+    // Update the interest
+    await $fetch('/api/update-interest', {
+      method: 'POST',
+      headers: {
+        'x-tag': xTagHeader,
+      },
+      body: {
+        id: interestId,
+        data: updateData
+      }
+    });
+    
+    return {
+      success: true,
+      document: documentData,
+      message: 'EOI document uploaded successfully',
+    };
+  } catch (error: any) {
+    console.error('Failed to upload EOI document:', error);
+    throw createError({
+      statusCode: 500,
+      statusMessage: error.message || 'Failed to upload EOI document',
+    });
+  }
+});
+
+async function getCurrentSalesLevel(interestId: string): Promise<string> {
+  try {
+    const interest = await $fetch(`/api/get-interest-by-id`, {
+      headers: {
+        'x-tag': '094ut234',
+      },
+      params: {
+        id: interestId,
+      },
+    });
+    return interest['Sales Process Level'] || '';
+  } catch (error) {
+    console.error('Failed to get current sales level:', error);
+    return '';
+  }
+}
+
+function shouldUpdateSalesLevel(currentLevel: string): boolean {
+  const levelsBeforeLOI = [
+    'General Qualified Interest',
+    'Specific Qualified Interest'
+  ];
+  return levelsBeforeLOI.includes(currentLevel);
+}
diff --git a/server/api/files/delete.ts b/server/api/files/delete.ts
index ce5eeaf..c1967e4 100644
--- a/server/api/files/delete.ts
+++ b/server/api/files/delete.ts
@@ -12,6 +12,14 @@ export default defineEventHandler(async (event) => {
       });
     }
     
+    // Protect EOIs folder from deletion
+    if (fileName === 'EOIs/' || fileName === 'EOIs') {
+      throw createError({
+        statusCode: 403,
+        statusMessage: 'The EOIs folder is protected and cannot be deleted',
+      });
+    }
+    
     // Delete folder or file based on type
     if (isFolder) {
       await deleteFolder(fileName);
diff --git a/server/api/files/proxy-download.ts b/server/api/files/proxy-download.ts
index 80eb61b..cc33afb 100644
--- a/server/api/files/proxy-download.ts
+++ b/server/api/files/proxy-download.ts
@@ -12,16 +12,44 @@ export default defineEventHandler(async (event) => {
       });
     }
     
-    // Get the download URL from MinIO
-    const url = await getDownloadUrl(fileName);
+    // Retry logic for getting download URL and fetching file
+    let response: Response | null = null;
+    let lastError: any = null;
     
-    // Fetch the file from MinIO
-    const response = await fetch(url);
+    for (let attempt = 0; attempt < 3; attempt++) {
+      try {
+        console.log(`[proxy-download] Attempting to download ${fileName} (attempt ${attempt + 1}/3)`);
+        
+        // Get the download URL from MinIO
+        const url = await getDownloadUrl(fileName);
+        
+        // Fetch the file from MinIO with timeout
+        const controller = new AbortController();
+        const timeout = setTimeout(() => controller.abort(), 30000); // 30 second timeout
+        
+        response = await fetch(url, { signal: controller.signal });
+        clearTimeout(timeout);
+        
+        if (response.ok) {
+          break; // Success, exit retry loop
+        }
+        
+        lastError = new Error(`HTTP ${response.status}: ${response.statusText}`);
+      } catch (error: any) {
+        lastError = error;
+        console.error(`[proxy-download] Attempt ${attempt + 1} failed:`, error.message);
+        
+        // Wait before retry with exponential backoff
+        if (attempt < 2) {
+          await new Promise(resolve => setTimeout(resolve, (attempt + 1) * 1000));
+        }
+      }
+    }
     
-    if (!response.ok) {
+    if (!response || !response.ok) {
       throw createError({
-        statusCode: response.status,
-        statusMessage: 'Failed to fetch file from storage',
+        statusCode: response?.status || 500,
+        statusMessage: lastError?.message || 'Failed to fetch file from storage after 3 attempts',
       });
     }
     
diff --git a/server/api/files/rename.ts b/server/api/files/rename.ts
index b4637b5..6966283 100644
--- a/server/api/files/rename.ts
+++ b/server/api/files/rename.ts
@@ -8,7 +8,15 @@ export default defineEventHandler(async (event) => {
     if (!oldName || !newName) {
       throw createError({
         statusCode: 400,
-        statusMessage: 'Old name and new name are required',
+        statusMessage: 'Both old and new names are required',
+      });
+    }
+    
+    // Protect EOIs folder from renaming
+    if (oldName === 'EOIs/' || oldName === 'EOIs') {
+      throw createError({
+        statusCode: 403,
+        statusMessage: 'The EOIs folder is protected and cannot be renamed',
       });
     }
     
diff --git a/server/plugins/eoi-reminders.ts b/server/plugins/eoi-reminders.ts
new file mode 100644
index 0000000..1b000c1
--- /dev/null
+++ b/server/plugins/eoi-reminders.ts
@@ -0,0 +1,19 @@
+import { scheduleEOIReminders } from '~/server/tasks/eoi-reminders';
+import { scheduleEmailProcessing } from '~/server/tasks/process-sales-emails';
+
+export default defineNitroPlugin((nitroApp) => {
+  // Schedule EOI reminders when server starts
+  console.log('[Plugin] Initializing EOI reminder scheduler...');
+  
+  // Add a small delay to ensure all services are ready
+  setTimeout(() => {
+    scheduleEOIReminders();
+  }, 5000);
+  
+  // Schedule email processing for EOI attachments
+  console.log('[Plugin] Initializing email processing scheduler...');
+  
+  setTimeout(() => {
+    scheduleEmailProcessing();
+  }, 7000);
+});
diff --git a/server/tasks/eoi-reminders.ts b/server/tasks/eoi-reminders.ts
new file mode 100644
index 0000000..4aa1283
--- /dev/null
+++ b/server/tasks/eoi-reminders.ts
@@ -0,0 +1,107 @@
+import cron from 'node-cron';
+import { getInterests } from '~/server/utils/nocodb';
+import { checkDocumentSignatureStatus } from '~/server/utils/documeso';
+
+// Track if tasks are already scheduled
+let tasksScheduled = false;
+
+export function scheduleEOIReminders() {
+  if (tasksScheduled) {
+    console.log('[EOI Reminders] Tasks already scheduled');
+    return;
+  }
+
+  console.log('[EOI Reminders] Scheduling reminder tasks...');
+
+  // Schedule for 9am daily
+  cron.schedule('0 9 * * *', async () => {
+    console.log('[EOI Reminders] Running 9am reminder check...');
+    await processReminders();
+  }, {
+    timezone: 'Europe/Paris'
+  });
+
+  // Schedule for 4pm daily
+  cron.schedule('0 16 * * *', async () => {
+    console.log('[EOI Reminders] Running 4pm reminder check...');
+    await processReminders();
+  }, {
+    timezone: 'Europe/Paris'
+  });
+
+  tasksScheduled = true;
+  console.log('[EOI Reminders] Tasks scheduled successfully');
+}
+
+async function processReminders() {
+  try {
+    // Get all interests
+    const response = await getInterests();
+    const interests = response.list || [];
+
+    console.log(`[EOI Reminders] Processing ${interests.length} interests...`);
+
+    for (const interest of interests) {
+      try {
+        // Skip if no document ID or reminders disabled
+        const documentId = (interest as any)['documeso_document_id'];
+        const remindersEnabled = (interest as any)['reminder_enabled'] !== false;
+        
+        if (!documentId || !remindersEnabled) {
+          continue;
+        }
+
+        // Check if we should send reminder (not sent in last 12 hours)
+        const lastReminderSent = (interest as any)['last_reminder_sent'];
+        if (lastReminderSent) {
+          const lastSentTime = new Date(lastReminderSent).getTime();
+          const twelveHoursAgo = Date.now() - (12 * 60 * 60 * 1000);
+          if (lastSentTime > twelveHoursAgo) {
+            continue; // Skip if reminder sent within last 12 hours
+          }
+        }
+
+        // Send reminder
+        await sendReminder(interest);
+      } catch (error) {
+        console.error(`[EOI Reminders] Error processing interest ${interest.Id}:`, error);
+      }
+    }
+
+    console.log('[EOI Reminders] Reminder processing completed');
+  } catch (error) {
+    console.error('[EOI Reminders] Error in processReminders:', error);
+  }
+}
+
+async function sendReminder(interest: any) {
+  try {
+    const response = await $fetch<{
+      success: boolean;
+      remindersSent: number;
+      results: any[];
+      message?: string;
+    }>('/api/eoi/send-reminders', {
+      method: 'POST',
+      headers: {
+        'x-tag': '094ut234' // System tag for automated processes
+      },
+      body: {
+        interestId: interest.Id.toString(),
+        documentId: (interest as any)['documeso_document_id']
+      }
+    });
+
+    if (response.success) {
+      console.log(`[EOI Reminders] Sent ${response.remindersSent} reminders for interest ${interest.Id}`);
+    }
+  } catch (error) {
+    console.error(`[EOI Reminders] Failed to send reminder for interest ${interest.Id}:`, error);
+  }
+}
+
+// Export function to manually trigger reminders (for testing)
+export async function triggerReminders() {
+  console.log('[EOI Reminders] Manually triggering reminder check...');
+  await processReminders();
+}
diff --git a/server/tasks/process-sales-emails.ts b/server/tasks/process-sales-emails.ts
new file mode 100644
index 0000000..0047f4e
--- /dev/null
+++ b/server/tasks/process-sales-emails.ts
@@ -0,0 +1,59 @@
+// Task to process sales emails for EOI documents
+import { $fetch } from 'ofetch';
+
+let taskScheduled = false;
+
+export function scheduleEmailProcessing() {
+  if (taskScheduled) {
+    console.log('[Process Sales Emails] Task already scheduled');
+    return;
+  }
+
+  console.log('[Process Sales Emails] Scheduling email processing task...');
+
+  // Process emails every 30 minutes
+  setInterval(async () => {
+    console.log('[Process Sales Emails] Running email check...');
+    await processEmails();
+  }, 30 * 60 * 1000); // 30 minutes
+
+  // Also run immediately on startup
+  setTimeout(() => {
+    processEmails();
+  }, 10000); // 10 seconds after startup
+
+  taskScheduled = true;
+  console.log('[Process Sales Emails] Task scheduled successfully');
+}
+
+async function processEmails() {
+  try {
+    const response = await $fetch('/api/email/process-sales-eois', {
+      method: 'POST',
+      headers: {
+        'x-tag': '094ut234' // System tag for automated processes
+      }
+    });
+
+    if (response.success) {
+      console.log(`[Process Sales Emails] Processed ${response.processed} emails`);
+      if (response.results && response.results.length > 0) {
+        response.results.forEach((result: any) => {
+          if (result.processed) {
+            console.log(`[Process Sales Emails] Successfully processed EOI for ${result.clientName}`);
+          } else {
+            console.log(`[Process Sales Emails] Failed to process EOI: ${result.error}`);
+          }
+        });
+      }
+    }
+  } catch (error) {
+    console.error('[Process Sales Emails] Error processing emails:', error);
+  }
+}
+
+// Export function to manually trigger processing (for testing)
+export async function triggerEmailProcessing() {
+  console.log('[Process Sales Emails] Manually triggering email processing...');
+  await processEmails();
+}
diff --git a/server/utils/documeso.ts b/server/utils/documeso.ts
new file mode 100644
index 0000000..9af1af6
--- /dev/null
+++ b/server/utils/documeso.ts
@@ -0,0 +1,153 @@
+// Documeso API client utilities
+interface DocumesoConfig {
+  apiUrl: string;
+  apiKey: string;
+}
+
+interface DocumesoRecipient {
+  id: number;
+  documentId: number;
+  email: string;
+  name: string;
+  role: 'SIGNER' | 'APPROVER' | 'VIEWER';
+  signingOrder: number;
+  token: string;
+  signedAt: string | null;
+  readStatus: 'NOT_OPENED' | 'OPENED';
+  signingStatus: 'NOT_SIGNED' | 'SIGNED';
+  sendStatus: 'NOT_SENT' | 'SENT';
+  signingUrl: string;
+}
+
+interface DocumesoDocument {
+  id: number;
+  externalId: string;
+  userId: number;
+  teamId: number;
+  title: string;
+  status: 'DRAFT' | 'PENDING' | 'COMPLETED' | 'CANCELLED';
+  documentDataId: string;
+  createdAt: string;
+  updatedAt: string;
+  completedAt: string | null;
+  recipients: DocumesoRecipient[];
+}
+
+interface DocumesoListResponse {
+  documents: DocumesoDocument[];
+  total: number;
+  page: number;
+  perPage: number;
+}
+
+// Get Documeso configuration
+const getDocumesoConfig = (): DocumesoConfig => {
+  return {
+    apiUrl: 'https://signatures.portnimara.dev/api/v1',
+    apiKey: 'Bearer api_malptg62zqyb0wrp'
+  };
+};
+
+// Fetch a single document by ID
+export const getDocumesoDocument = async (documentId: number): Promise<DocumesoDocument> => {
+  const config = getDocumesoConfig();
+  
+  try {
+    const response = await $fetch<DocumesoDocument>(`${config.apiUrl}/documents/${documentId}`, {
+      headers: {
+        'Authorization': config.apiKey,
+        'Content-Type': 'application/json'
+      }
+    });
+    
+    return response;
+  } catch (error) {
+    console.error('Failed to fetch Documeso document:', error);
+    throw error;
+  }
+};
+
+// Search documents by external ID (e.g., 'loi-94')
+export const searchDocumesoDocuments = async (externalId?: string): Promise<DocumesoDocument[]> => {
+  const config = getDocumesoConfig();
+  
+  try {
+    const response = await $fetch<DocumesoListResponse>(`${config.apiUrl}/documents`, {
+      headers: {
+        'Authorization': config.apiKey,
+        'Content-Type': 'application/json'
+      },
+      params: {
+        perPage: 100
+      }
+    });
+    
+    // If externalId is provided, filter by it
+    if (externalId) {
+      return response.documents.filter(doc => doc.externalId === externalId);
+    }
+    
+    return response.documents;
+  } catch (error) {
+    console.error('Failed to search Documeso documents:', error);
+    throw error;
+  }
+};
+
+// Get document by external ID (e.g., 'loi-94')
+export const getDocumesoDocumentByExternalId = async (externalId: string): Promise<DocumesoDocument | null> => {
+  const documents = await searchDocumesoDocuments(externalId);
+  return documents.length > 0 ? documents[0] : null;
+};
+
+// Check signature status for a document
+export const checkDocumentSignatureStatus = async (documentId: number): Promise<{
+  documentStatus: string;
+  unsignedRecipients: DocumesoRecipient[];
+  signedRecipients: DocumesoRecipient[];
+  clientSigned: boolean;
+  allSigned: boolean;
+}> => {
+  const document = await getDocumesoDocument(documentId);
+  
+  const unsignedRecipients = document.recipients.filter(r => r.signingStatus === 'NOT_SIGNED');
+  const signedRecipients = document.recipients.filter(r => r.signingStatus === 'SIGNED');
+  
+  // Check if client (signingOrder = 1) has signed
+  const clientRecipient = document.recipients.find(r => r.signingOrder === 1);
+  const clientSigned = clientRecipient ? clientRecipient.signingStatus === 'SIGNED' : false;
+  
+  const allSigned = unsignedRecipients.length === 0;
+  
+  return {
+    documentStatus: document.status,
+    unsignedRecipients,
+    signedRecipients,
+    clientSigned,
+    allSigned
+  };
+};
+
+// Get recipients who need to sign (excluding client)
+export const getRecipientsToRemind = async (documentId: number): Promise<DocumesoRecipient[]> => {
+  const status = await checkDocumentSignatureStatus(documentId);
+  
+  // Only remind if client has signed
+  if (!status.clientSigned) {
+    return [];
+  }
+  
+  // Return unsigned recipients with signingOrder > 1
+  return status.unsignedRecipients.filter(r => r.signingOrder > 1);
+};
+
+// Format recipient name for emails
+export const formatRecipientName = (recipient: DocumesoRecipient): string => {
+  const firstName = recipient.name.split(' ')[0];
+  return firstName;
+};
+
+// Get signing URL for a recipient
+export const getSigningUrl = (recipient: DocumesoRecipient): string => {
+  return recipient.signingUrl;
+};
diff --git a/server/utils/email-utils.ts b/server/utils/email-utils.ts
new file mode 100644
index 0000000..2b21ac2
--- /dev/null
+++ b/server/utils/email-utils.ts
@@ -0,0 +1,81 @@
+import { simpleParser } from 'mailparser';
+import type { ParsedMail } from 'mailparser';
+import Imap from 'imap';
+
+export type { ParsedMail };
+
+export interface EmailCredentials {
+  user: string;
+  password: string;
+  host: string;
+  port: number;
+  tls: boolean;
+}
+
+export async function parseEmail(emailContent: string): Promise<ParsedMail> {
+  return await simpleParser(emailContent);
+}
+
+export function getIMAPConnection(credentials: EmailCredentials): Promise<Imap> {
+  return new Promise((resolve, reject) => {
+    const imap = new Imap({
+      user: credentials.user,
+      password: credentials.password,
+      host: credentials.host,
+      port: credentials.port,
+      tls: credentials.tls,
+      tlsOptions: { rejectUnauthorized: false }
+    });
+
+    imap.once('ready', () => {
+      console.log('[IMAP] Connection ready');
+      resolve(imap);
+    });
+
+    imap.once('error', (err: Error) => {
+      console.error('[IMAP] Connection error:', err);
+      reject(err);
+    });
+
+    imap.connect();
+  });
+}
+
+export function searchEmails(imap: Imap, criteria: any[]): Promise<number[]> {
+  return new Promise((resolve, reject) => {
+    imap.search(criteria, (err: Error | null, results: number[]) => {
+      if (err) reject(err);
+      else resolve(results || []);
+    });
+  });
+}
+
+export function fetchEmail(imap: Imap, msgId: number, options: any): Promise<string> {
+  return new Promise((resolve, reject) => {
+    let emailData = '';
+    
+    const fetch = imap.fetch(msgId, options);
+    
+    fetch.on('message', (msg: any) => {
+      msg.on('body', (stream: any) => {
+        stream.on('data', (chunk: Buffer) => {
+          emailData += chunk.toString();
+        });
+        
+        stream.once('end', () => {
+          resolve(emailData);
+        });
+      });
+    });
+    
+    fetch.once('error', (err: Error) => {
+      reject(err);
+    });
+    
+    fetch.once('end', () => {
+      if (!emailData) {
+        reject(new Error('No email data received'));
+      }
+    });
+  });
+}
diff --git a/server/utils/email.ts b/server/utils/email.ts
new file mode 100644
index 0000000..d7b61b4
--- /dev/null
+++ b/server/utils/email.ts
@@ -0,0 +1,45 @@
+import nodemailer from 'nodemailer';
+
+interface EmailOptions {
+  from: string;
+  to: string;
+  subject: string;
+  html?: string;
+  text?: string;
+}
+
+interface SmtpConfig {
+  host: string;
+  port: number;
+  secure: boolean;
+  auth: {
+    user: string;
+    pass: string;
+  };
+}
+
+export async function sendEmail(options: EmailOptions, config?: SmtpConfig) {
+  // Use provided config or default to environment config
+  const smtpConfig = config || {
+    host: process.env.SMTP_HOST || 'mail.portnimara.com',
+    port: parseInt(process.env.SMTP_PORT || '465'),
+    secure: process.env.SMTP_SECURE !== 'false',
+    auth: {
+      user: process.env.SMTP_USER || '',
+      pass: process.env.SMTP_PASS || ''
+    }
+  };
+
+  // Create transporter
+  const transporter = nodemailer.createTransport(smtpConfig);
+
+  // Send email
+  try {
+    const info = await transporter.sendMail(options);
+    console.log('Email sent:', info.messageId);
+    return info;
+  } catch (error) {
+    console.error('Failed to send email:', error);
+    throw error;
+  }
+}
diff --git a/server/utils/minio.ts b/server/utils/minio.ts
index c948c80..76ec8d3 100644
--- a/server/utils/minio.ts
+++ b/server/utils/minio.ts
@@ -297,3 +297,21 @@ export const renameFolder = async (oldPath: string, newPath: string) => {
     });
   });
 };
+
+// Create bucket if it doesn't exist
+export const createBucketIfNotExists = async (bucketName?: string) => {
+  const client = getMinioClient();
+  const bucket = bucketName || useRuntimeConfig().minio.bucketName;
+  
+  try {
+    const exists = await client.bucketExists(bucket);
+    if (!exists) {
+      await client.makeBucket(bucket);
+      console.log(`Bucket '${bucket}' created successfully`);
+    }
+    return true;
+  } catch (error) {
+    console.error('Error creating bucket:', error);
+    throw error;
+  }
+};
diff --git a/server/utils/nocodb.ts b/server/utils/nocodb.ts
index b95fa02..3d79a59 100644
--- a/server/utils/nocodb.ts
+++ b/server/utils/nocodb.ts
@@ -299,3 +299,34 @@ export const triggerWebhook = async (url: string, payload: any) =>
     method: "POST",
     body: payload,
   });
+
+export const updateInterestEOIDocument = async (id: string, documentData: any) => {
+  console.log('[nocodb.updateInterestEOIDocument] Updating EOI document for interest:', id);
+  
+  // Get existing EOI Document array or create new one
+  const interest = await getInterestById(id);
+  const existingDocuments = interest['EOI Document'] || [];
+  
+  // Add the new document to the array
+  const updatedDocuments = [...existingDocuments, documentData];
+  
+  // Update the interest with the new EOI Document array
+  return updateInterest(id, {
+    'EOI Document': updatedDocuments
+  });
+};
+
+export const getInterestByFieldAsync = async (fieldName: string, value: any): Promise<Interest | null> => {
+  try {
+    const response = await getInterests();
+    const interests = response.list || [];
+    
+    // Find interest where the field matches the value
+    const interest = interests.find(i => (i as any)[fieldName] === value);
+    
+    return interest || null;
+  } catch (error) {
+    console.error('Error fetching interest by field:', error);
+    return null;
+  }
+};