diff --git a/frontend/dashboard.js b/frontend/dashboard.js
index 39ec8ee..2822436 100644
--- a/frontend/dashboard.js
+++ b/frontend/dashboard.js
@@ -714,11 +714,23 @@
         'Session recovery could not be saved on this device. You can keep working.';
     },
   });
+  function updateDetailDeferLabels(active) {
+    document.querySelectorAll('[data-detail-defer-preset=today]').forEach(button => {
+      button.textContent = active ? 'Later today & next' : 'Later today';
+    });
+    document.querySelectorAll('[data-detail-defer-preset=tomorrow]').forEach(button => {
+      button.textContent = active ? 'Tomorrow & next' : 'Tomorrow';
+    });
+    document.querySelectorAll('[data-detail-defer-custom]').forEach(button => {
+      button.textContent = active ? 'Choose date & time & next' : 'Choose date & time';
+    });
+  }
   function updateWorkSessionActions() {
     const active = workSession.active();
     qs('#start-work-session').hidden = active;
     qs('#resume-today-session').hidden = active || !todayMyWork.length || !workSession.resumable();
     qs('#end-today-session').hidden = !active;
+    updateDetailDeferLabels(active);
     mobileTaskDock.updateWork(mobileWorkEntry.mode(), countMyWork(activeMyWork).attention);
   }
 
@@ -1238,6 +1250,10 @@
   const detailDefer = createDetailDefer({
     laterWork,
     session: workSession,
+    continueSession: item => completeTodayItem(item, {
+      successMessage: 'Deferred to Later. Next Today item opened.',
+      failureMessage: 'Could not remove this item from Today.',
+    }),
     close: () => workRoute.close(),
     refresh: refreshMyWorkView,
     focus: () => qs('[data-work-filter="' + selectedWorkFilter + '"]')?.focus(),
diff --git a/frontend/detail-defer.js b/frontend/detail-defer.js
index b7a3ebd..4f70830 100644
--- a/frontend/detail-defer.js
+++ b/frontend/detail-defer.js
@@ -1,6 +1,7 @@
 function createDetailDefer({
   laterWork,
   session,
+  continueSession = null,
   close,
   refresh,
   focus,
@@ -16,6 +17,13 @@ function createDetailDefer({
         return false;
       }
       const inSession = session.active();
+      if (continueSession && session.checkpointed?.(item)) {
+        if (continueSession(item) === true) return true;
+        laterWork.restore(item);
+        refresh();
+        announce('Could not remove this item from Today, so it was restored from Later.');
+        return false;
+      }
       if (!inSession && closeSheet) close();
       refresh();
       announce('Deferred until ' + formatTime(until) + '. It stays unread and unchanged in Gitea.');
diff --git a/tests/test_my_work.py b/tests/test_my_work.py
index f911a6e..ddfec1e 100644
--- a/tests/test_my_work.py
+++ b/tests/test_my_work.py
@@ -1223,6 +1223,75 @@ process.stdout.write(JSON.stringify({{saved,calls}}));
     }
 
 
+def test_detail_defer_completes_checkpointed_today_item_after_saving_later():
+    script = f"""
+const createDetailDefer = require({json.dumps(str(DETAIL_DEFER))});
+const calls = [];
+const item = {{kind:'issue',repository:'stackchain/api',number:17,title:'Read first'}};
+const controller = createDetailDefer({{
+  laterWork: {{
+    presetUntil:() => new Date('2026-08-09T09:00:00Z'),
+    defer:(saved, until) => {{ calls.push(['defer', saved.title, until.toISOString()]); return 'deferred'; }},
+    restore:() => calls.push(['restore']),
+  }},
+  session: {{active:() => true, checkpointed:saved => saved === item}},
+  continueSession:saved => {{ calls.push(['continue', saved.title]); return true; }},
+  close:() => calls.push(['close']), refresh:() => calls.push(['refresh']),
+  focus:() => calls.push(['focus']), announce:message => calls.push(['announce', message]),
+}});
+const saved = controller.defer(item, 'tomorrow');
+process.stdout.write(JSON.stringify({{saved,calls}}));
+"""
+
+    result = subprocess.run(
+        ["node", "-e", script], check=True, capture_output=True, text=True
+    )
+
+    assert json.loads(result.stdout) == {
+        "saved": True,
+        "calls": [
+            ["defer", "Read first", "2026-08-09T09:00:00.000Z"],
+            ["continue", "Read first"],
+        ],
+    }
+
+
+def test_detail_defer_rolls_back_later_when_today_cannot_be_removed():
+    script = f"""
+const createDetailDefer = require({json.dumps(str(DETAIL_DEFER))});
+const calls = [];
+const item = {{kind:'issue',repository:'stackchain/api',number:17}};
+const controller = createDetailDefer({{
+  laterWork: {{
+    presetUntil:() => new Date('2026-08-09T09:00:00Z'),
+    defer:() => {{ calls.push('defer'); return 'deferred'; }},
+    restore:saved => {{ calls.push(['restore', saved.number]); return true; }},
+  }},
+  session: {{active:() => true, checkpointed:() => true}},
+  continueSession:() => {{ calls.push('continue'); return false; }},
+  close:() => calls.push('close'), refresh:() => calls.push('refresh'),
+  focus:() => calls.push('focus'), announce:message => calls.push(['announce', message]),
+}});
+const saved = controller.defer(item, 'tomorrow');
+process.stdout.write(JSON.stringify({{saved,calls}}));
+"""
+
+    result = subprocess.run(
+        ["node", "-e", script], check=True, capture_output=True, text=True
+    )
+
+    assert json.loads(result.stdout) == {
+        "saved": False,
+        "calls": [
+            "defer",
+            "continue",
+            ["restore", 17],
+            "refresh",
+            ["announce", "Could not remove this item from Today, so it was restored from Later."],
+        ],
+    }
+
+
 @pytest.mark.anyio
 async def test_mobile_detail_sheets_offer_touch_safe_defer_without_a_gitea_mutation():
     html = await dashboard()
@@ -1238,6 +1307,18 @@ async def test_mobile_detail_sheets_offer_touch_safe_defer_without_a_gitea_mutat
     assert "fetch(" not in DETAIL_DEFER.read_text()
 
 
+@pytest.mark.anyio
+async def test_checkpointed_detail_defer_completes_today_and_advertises_next_item():
+    html = await dashboard()
+
+    assert "continueSession: item => completeTodayItem(item, {" in html
+    assert "successMessage: 'Deferred to Later. Next Today item opened.'" in html
+    assert "advance: () => runTodayTransition('complete')" in html
+    assert "button.textContent = active ? 'Later today & next' : 'Later today'" in html
+    assert "button.textContent = active ? 'Tomorrow & next' : 'Tomorrow'" in html
+    assert "button.textContent = active ? 'Choose date & time & next' : 'Choose date & time'" in html
+
+
 @pytest.mark.anyio
 async def test_mobile_my_work_wires_touch_safe_non_mutating_later_actions():
     html = await dashboard()