diff --git a/src/components/interests/interest-tabs.tsx b/src/components/interests/interest-tabs.tsx
index 093f223a..f211e309 100644
--- a/src/components/interests/interest-tabs.tsx
+++ b/src/components/interests/interest-tabs.tsx
@@ -63,7 +63,13 @@ type InterestPatchField =
   | 'source'
   | 'desiredLengthFt'
   | 'desiredWidthFt'
-  | 'desiredDraftFt';
+  | 'desiredDraftFt'
+  | 'dateEoiSent'
+  | 'dateEoiSigned'
+  | 'dateReservationSigned'
+  | 'dateDepositReceived'
+  | 'dateContractSent'
+  | 'dateContractSigned';
 
 const LEAD_CATEGORY_OPTIONS = LEAD_CATEGORIES.map((c) => ({
   value: c,
@@ -347,6 +353,72 @@ function MilestoneAdvanceButton({
   );
 }
 
+/**
+ * Skip-ahead backfill control: shown next to past milestones whose
+ * date column is null. Opens the same date popover as
+ * MilestoneAdvanceButton but PATCHes the date column directly without
+ * triggering a stage transition — the stage was already advanced
+ * manually upstream.
+ */
+function MilestoneBackfillButton({
+  label,
+  disabled,
+  onConfirm,
+}: {
+  label: string;
+  disabled?: boolean;
+  onConfirm: (milestoneDate: string) => void | Promise<void>;
+}) {
+  const [open, setOpen] = useState(false);
+  const [date, setDate] = useState<string>(() => new Date().toISOString().slice(0, 10));
+  return (
+    <Popover open={open} onOpenChange={setOpen}>
+      <PopoverTrigger asChild>
+        <button
+          type="button"
+          disabled={disabled}
+          className="text-xs font-medium text-primary hover:underline disabled:opacity-50"
+        >
+          {label}
+        </button>
+      </PopoverTrigger>
+      <PopoverContent align="start" className="w-64 space-y-2 p-3">
+        <div className="space-y-1">
+          <label className="text-xs font-medium" htmlFor="backfill-date">
+            Date completed
+          </label>
+          <DatePicker
+            id="backfill-date"
+            value={date}
+            toDate={new Date()}
+            onChange={setDate}
+            placeholder="Pick a date"
+          />
+          <p className="text-[11px] text-muted-foreground">
+            Records the date the milestone happened. Does not change the deal&apos;s pipeline stage.
+          </p>
+        </div>
+        <div className="flex justify-end gap-2">
+          <Button type="button" variant="ghost" size="sm" onClick={() => setOpen(false)}>
+            Cancel
+          </Button>
+          <Button
+            type="button"
+            size="sm"
+            disabled={!date || disabled}
+            onClick={async () => {
+              await onConfirm(date);
+              setOpen(false);
+            }}
+          >
+            Save date
+          </Button>
+        </div>
+      </PopoverContent>
+    </Popover>
+  );
+}
+
 function MilestoneSection({
   title,
   icon: Icon,
@@ -616,10 +688,37 @@ function OverviewTab({
   } as const;
   const order = ['berth_interest', 'eoi', 'reservation', 'deposit', 'contract'] as const;
   const firstIncompleteKey = order.find((k) => !milestoneCompletion[k]) ?? null;
+  // 2026-05-21: a "stage-owning" milestone is the one that maps 1:1 with
+  // the deal's current pipelineStage column. When the rep manually
+  // jumps the stage forward (Reservation+) but earlier sub-statuses
+  // are still un-signed, we need the current-stage milestone to stay
+  // marked `'current'` regardless of completion — otherwise EOI gets
+  // flagged as NEXT STEP and the actual current stage hides under
+  // "Upcoming milestones". Earlier-than-stage milestones go to
+  // `'past'` so the rep can render backfill controls against them.
+  const STAGE_TO_MILESTONE: Partial<Record<PipelineStage, (typeof order)[number]>> = {
+    eoi: 'eoi',
+    reservation: 'reservation',
+    deposit_paid: 'deposit',
+    contract: 'contract',
+  };
+  const stageOwnedMilestone = STAGE_TO_MILESTONE[interest.pipelineStage as PipelineStage] ?? null;
+  const stageOwnedIdx = stageOwnedMilestone ? order.indexOf(stageOwnedMilestone) : -1;
   const phaseFor = (k: (typeof order)[number]): Phase => {
-    if (milestoneCompletion[k]) return 'past';
-    if (k === firstIncompleteKey) return 'current';
-    return 'future';
+    // Stage owns this milestone → always current, never collapsed.
+    if (stageOwnedMilestone === k) return 'current';
+    // Otherwise: completion drives past/future ordering when no stage
+    // owns a milestone (enquiry/qualified/nurturing stages).
+    if (!stageOwnedMilestone) {
+      if (milestoneCompletion[k]) return 'past';
+      if (k === firstIncompleteKey) return 'current';
+      return 'future';
+    }
+    // A stage DOES own a different milestone — bucket by position
+    // relative to it. Earlier slots go to `past` even if incomplete
+    // (the backfill controls live there); later slots go to `future`.
+    const idx = order.indexOf(k);
+    return idx < stageOwnedIdx ? 'past' : 'future';
   };
   const berthInterestPhase: Phase = phaseFor('berth_interest');
   const eoiPhase: Phase = phaseFor('eoi');
@@ -730,9 +829,20 @@ function OverviewTab({
             </Button>
           </div>
         ) : null,
-      pastSummary: interest.dateEoiSigned
-        ? `Signed ${formatDate(interest.dateEoiSigned)}`
-        : 'Completed',
+      pastSummary: interest.dateEoiSigned ? (
+        `Signed ${formatDate(interest.dateEoiSigned)}`
+      ) : (
+        <span className="inline-flex items-center gap-1.5">
+          <span>Completed</span>
+          <MilestoneBackfillButton
+            label="Set date"
+            disabled={mutation.isPending}
+            onConfirm={async (d) => {
+              await mutation.mutateAsync({ dateEoiSigned: d });
+            }}
+          />
+        </span>
+      ),
     },
     {
       key: 'reservation',
@@ -748,9 +858,20 @@ function OverviewTab({
           actionLabel: 'Mark reservation as signed',
         },
       ],
-      pastSummary: interest.dateReservationSigned
-        ? `Signed ${formatDate(interest.dateReservationSigned)}`
-        : 'Completed',
+      pastSummary: interest.dateReservationSigned ? (
+        `Signed ${formatDate(interest.dateReservationSigned)}`
+      ) : (
+        <span className="inline-flex items-center gap-1.5">
+          <span>Completed</span>
+          <MilestoneBackfillButton
+            label="Set date"
+            disabled={mutation.isPending}
+            onConfirm={async (d) => {
+              await mutation.mutateAsync({ dateReservationSigned: d });
+            }}
+          />
+        </span>
+      ),
     },
     {
       key: 'deposit',
@@ -780,9 +901,20 @@ function OverviewTab({
             </span>
           </div>
         ) : null,
-      pastSummary: interest.dateDepositReceived
-        ? `Received ${formatDate(interest.dateDepositReceived)}`
-        : 'Recorded',
+      pastSummary: interest.dateDepositReceived ? (
+        `Received ${formatDate(interest.dateDepositReceived)}`
+      ) : (
+        <span className="inline-flex items-center gap-1.5">
+          <span>Recorded</span>
+          <MilestoneBackfillButton
+            label="Set date"
+            disabled={mutation.isPending}
+            onConfirm={async (d) => {
+              await mutation.mutateAsync({ dateDepositReceived: d });
+            }}
+          />
+        </span>
+      ),
     },
     {
       key: 'contract',
@@ -804,9 +936,20 @@ function OverviewTab({
           actionLabel: 'Mark contract as signed',
         },
       ],
-      pastSummary: interest.dateContractSigned
-        ? `Signed ${formatDate(interest.dateContractSigned)}`
-        : 'Completed',
+      pastSummary: interest.dateContractSigned ? (
+        `Signed ${formatDate(interest.dateContractSigned)}`
+      ) : (
+        <span className="inline-flex items-center gap-1.5">
+          <span>Completed</span>
+          <MilestoneBackfillButton
+            label="Set date"
+            disabled={mutation.isPending}
+            onConfirm={async (d) => {
+              await mutation.mutateAsync({ dateContractSigned: d });
+            }}
+          />
+        </span>
+      ),
     },
   ];
 
diff --git a/src/lib/validators/interests.ts b/src/lib/validators/interests.ts
index bdb85198..3e4b5bb6 100644
--- a/src/lib/validators/interests.ts
+++ b/src/lib/validators/interests.ts
@@ -63,6 +63,7 @@ export const createInterestSchema = z.object({
   dateEoiSent: z.coerce.date().nullable().optional(),
   dateEoiSigned: z.coerce.date().nullable().optional(),
   dateReservationSigned: z.coerce.date().nullable().optional(),
+  dateDepositReceived: z.coerce.date().nullable().optional(),
   dateContractSent: z.coerce.date().nullable().optional(),
   dateContractSigned: z.coerce.date().nullable().optional(),
   pipelineStage: z.enum(PIPELINE_STAGES).default('enquiry'),