diff --git a/client/src/components/shared/CustomDateTimePicker.test.tsx b/client/src/components/shared/CustomDateTimePicker.test.tsx
index 986e2419e..d3f741d4e 100644
--- a/client/src/components/shared/CustomDateTimePicker.test.tsx
+++ b/client/src/components/shared/CustomDateTimePicker.test.tsx
@@ -577,9 +577,12 @@ describe('CustomDatePicker branches', () => {
       render(<CustomDatePicker value="2026-03-15" onChange={onChange} />);
       openCalendar();
       const dialog = screen.getByRole('dialog');
-      // vw < 360 centres the 268px popup; the popup flips above the trigger
+      // vw < 360 centres the 268px popup; the popup flips above the trigger,
+      // anchored from the trigger's own top edge via `bottom` (not a `top`
+      // computed by subtracting a guessed popup height — see FE-W5DP-024).
       expect(dialog.style.left).toBe('26px');
-      expect(dialog.style.top).toBe('336px');
+      expect(dialog.style.top).toBe('');
+      expect(dialog.style.bottom).toBe('72px');
     } finally {
       Element.prototype.getBoundingClientRect = originalRect;
       Object.defineProperty(window, 'innerWidth', { value: originalWidth, configurable: true });
@@ -605,6 +608,31 @@ describe('CustomDatePicker branches', () => {
     }
   });
 
+  it('FE-W5DP-024: a flipped popup stays flush against its trigger instead of a fixed guessed offset (#2334)', () => {
+    // A settle-up-style form: the trigger sits low enough that the popup can't
+    // fit below it, but there is plenty of room above — a shorter gap than the
+    // worst-case guess would previously leave the popup floating over unrelated
+    // fields higher up the form instead of right above its own trigger.
+    const originalRect = Element.prototype.getBoundingClientRect;
+    Element.prototype.getBoundingClientRect = function () {
+      return { left: 440, top: 529, right: 803, bottom: 566, width: 363, height: 37, x: 440, y: 529, toJSON: () => ({}) } as DOMRect;
+    };
+
+    try {
+      render(<CustomDatePicker value="2026-03-15" onChange={onChange} />);
+      openCalendar();
+      const dialog = screen.getByRole('dialog');
+      // jsdom's default innerHeight (768) leaves 768-566=202px below the
+      // trigger — short of the flip threshold — so it flips, anchored to the
+      // trigger's own top edge (768-529+4=243), not a `top` derived from
+      // subtracting a guessed popup height.
+      expect(dialog.style.top).toBe('');
+      expect(dialog.style.bottom).toBe('243px');
+    } finally {
+      Element.prototype.getBoundingClientRect = originalRect;
+    }
+  });
+
   it('FE-W5DP-018: the header arrows and the label highlight on hover', () => {
     render(<CustomDatePicker value="2026-03-15" onChange={onChange} />);
     openCalendar();
diff --git a/client/src/components/shared/CustomDateTimePicker.tsx b/client/src/components/shared/CustomDateTimePicker.tsx
index 2c8436b23..2d189aaf7 100644
--- a/client/src/components/shared/CustomDateTimePicker.tsx
+++ b/client/src/components/shared/CustomDateTimePicker.tsx
@@ -383,22 +383,30 @@ export function CustomDatePicker({
               position: 'fixed',
               // reanchor ticks on scroll / resize / keyboard so this recomputes
               // against a fresh rect instead of the one measured on open (#1999).
-              ...((): { top: number; left: number } => {
+              ...((): { top?: number; bottom?: number; left: number } => {
                 void reanchor;
                 const r = ref.current?.getBoundingClientRect();
                 if (!r) return { top: 0, left: 0 };
                 const w = 268,
                   pad = 8,
+                  // Only used to decide *whether* the popup fits below the trigger —
+                  // its real height varies with the month's row count and the view
+                  // (days/months/years), so it can't be known before it renders.
                   h = 360;
                 const vw = window.innerWidth;
                 const vh = window.visualViewport?.height ?? window.innerHeight;
                 let left = r.left;
-                let top = r.bottom + 4;
                 if (left + w > vw - pad) left = Math.max(pad, vw - w - pad);
-                if (top + h > vh - pad) top = r.top - h - 4;
-                top = Math.max(pad, Math.min(top, vh - h - pad));
                 if (vw < 360) left = Math.max(pad, (vw - w) / 2);
-                return { top, left };
+                if (r.bottom + 4 + h <= vh - pad) return { top: r.bottom + 4, left };
+                // Flipped: anchor from the trigger's own top edge via `bottom`
+                // instead of subtracting a guessed height from `top`. A guessed
+                // `top` leaves a gap sized by however wrong the guess was — in a
+                // short modal (e.g. the settle-up form) that gap was big enough to
+                // land the popup over unrelated fields instead of the trigger it
+                // belongs to. Anchoring the opposite edge means the popup always
+                // sits flush against the trigger no matter its real height.
+                return { bottom: Math.max(pad, vh - r.top + 4), left };
               })(),
               zIndex: 99999,
               background: 'var(--bg-card)',