diff --git a/frontend/dashboard.js b/frontend/dashboard.js
index 1a4e850..9a13d51 100644
--- a/frontend/dashboard.js
+++ b/frontend/dashboard.js
@@ -7331,6 +7331,9 @@
     flushAuthored: flushAuthoredOutbox,
     flushNotificationReads: flushNotificationReadOutbox,
   });
+  const reconnectAfterOnline = () => setTimeout(reconnectOutboxes, 500);
+  window.addEventListener('online', reconnectAfterOnline);
+  workspaceLifecycle.replayOnline(reconnectAfterOnline);
   async function setOfflineWorkEnabled(enabled) {
     keepWorkOffline.checked = enabled;
     offlineWorkStore.setEnabled(enabled);
@@ -7388,9 +7391,6 @@
   updateDeliveryReceiptControls();
   if (!navigator.onLine) await showOfflineStatus();
   window.addEventListener('offline', showOfflineStatus);
-  const reconnectAfterOnline = () => setTimeout(reconnectOutboxes, 500);
-  window.addEventListener('online', reconnectAfterOnline);
-  workspaceLifecycle.replayOnline(reconnectAfterOnline);
 
   qs('#refresh').addEventListener('click', load);
   qs('#plan-today').addEventListener('click', event => openPlanToday(event.currentTarget));
diff --git a/frontend/reconnect-outboxes.js b/frontend/reconnect-outboxes.js
index 85f1fd2..e304299 100644
--- a/frontend/reconnect-outboxes.js
+++ b/frontend/reconnect-outboxes.js
@@ -5,7 +5,10 @@ function createReconnectOutboxes({
   flushAuthored,
   flushNotificationReads,
 }) {
-  return async function reconnectOutboxes() {
+  let activeReconnect = null;
+  let followUpRequested = false;
+
+  async function reconnectOnce() {
     const snapshot = await refresh();
     const freshness = snapshot?.freshness?.sections?.context;
     const identityFresh = snapshot?.context && !snapshot.context.error &&
@@ -19,6 +22,22 @@ function createReconnectOutboxes({
       flushNotificationReads(),
     ]);
     return true;
+  }
+
+  return function reconnectOutboxes() {
+    if (activeReconnect) {
+      followUpRequested = true;
+      return activeReconnect;
+    }
+    activeReconnect = (async () => {
+      let result = false;
+      do {
+        followUpRequested = false;
+        result = await reconnectOnce();
+      } while (followUpRequested);
+      return result;
+    })().finally(() => { activeReconnect = null; });
+    return activeReconnect;
   };
 }
 
diff --git a/frontend/workspace-bootstrap.js b/frontend/workspace-bootstrap.js
index 7698292..7a56902 100644
--- a/frontend/workspace-bootstrap.js
+++ b/frontend/workspace-bootstrap.js
@@ -25,9 +25,14 @@ async function loadWorkspace({ document, window = null, createLoader = createFea
     };
   } catch (error) {
     window?.removeEventListener('online', captureOnline);
+    if (window?.location?.reload) {
+      if (cameOnline) window.location.reload();
+      else window.addEventListener('online', () => window.location.reload(), { once: true });
+    }
     if (status) {
-      status.textContent =
-        'Workspace could not load. Check your connection, then reload to retry.';
+      status.textContent = window
+        ? 'Workspace could not load. Reconnect to retry automatically, or reload now.'
+        : 'Workspace could not load. Check your connection, then reload to retry.';
     }
     throw error;
   }
diff --git a/tests/e2e/test_mobile_offline_issue_release.py b/tests/e2e/test_mobile_offline_issue_release.py
index ae20ea2..2ad2bbd 100644
--- a/tests/e2e/test_mobile_offline_issue_release.py
+++ b/tests/e2e/test_mobile_offline_issue_release.py
@@ -275,7 +275,19 @@ def test_release_artifact_files_one_mobile_issue_exactly_once_after_offline_relo
                 if fake.created_issues:
                     break
                 page.wait_for_timeout(250)
-            assert fake.created_issues == [{"title": TITLE, "body": BODY, "assignee": "timmy"}]
+            assert fake.created_issues == [
+                {"title": TITLE, "body": BODY, "assignee": "timmy"}
+            ], (
+                f"url={page.url} ready={page.evaluate('document.readyState')} "
+                f"status={page.locator('#my-work-action-status').inner_text()!r} "
+                f"errors={browser_errors[-5:]!r} responses={failed_responses[-10:]!r} "
+                f"requests={fake.requests[-20:]!r}"
+            )
+            # Deferred workspace startup can report its already-issued offline request
+            # after the pre-reconnect clear; retain every non-offline browser error.
+            browser_errors[:] = [
+                error for error in browser_errors if "ERR_INTERNET_DISCONNECTED" not in error
+            ]
 
             for _ in range(40):
                 durable_completion = indexed_issue_records(page)
diff --git a/tests/test_reconnect_outboxes.py b/tests/test_reconnect_outboxes.py
index 01485dc..969da9e 100644
--- a/tests/test_reconnect_outboxes.py
+++ b/tests/test_reconnect_outboxes.py
@@ -41,6 +41,36 @@ reconnect().then(result => process.stdout.write(JSON.stringify({{result, calls}}
     }
 
 
+def test_concurrent_reconnect_requests_queue_one_follow_up_flush():
+    result = run_node(
+        f"""
+const createReconnectOutboxes = require({json.dumps(str(RECONNECT))});
+(async () => {{
+let releaseFirst; let issueCalls=0; let active=0; let maxActive=0;
+const reconnect = createReconnectOutboxes({{
+  refresh: async () => ({{context:{{user:{{login:'timmy'}}}}}}),
+  restoreIdentity: () => {{}},
+  flushIssue: async () => {{
+    issueCalls++; active++; maxActive=Math.max(maxActive,active);
+    if (issueCalls === 1) await new Promise(resolve => {{ releaseFirst=resolve; }});
+    active--;
+  }},
+  flushAuthored: async () => {{}},
+  flushNotificationReads: async () => {{}},
+}});
+const first=reconnect();
+while (!releaseFirst) await new Promise(resolve=>setTimeout(resolve,0));
+const second=reconnect();
+releaseFirst();
+await Promise.all([first,second]);
+process.stdout.write(JSON.stringify({{issueCalls,maxActive}}));
+}})().catch(error => {{ console.error(error); process.exit(1); }});
+"""
+    )
+
+    assert result == {"issueCalls": 2, "maxActive": 1}
+
+
 def test_dashboard_uses_reconnect_flush_after_live_identity_refresh():
     index = (ROOT / "frontend" / "index.html").read_text()
     dashboard = (ROOT / "frontend" / "dashboard.js").read_text()
@@ -50,3 +80,12 @@ def test_dashboard_uses_reconnect_flush_after_live_identity_refresh():
     assert "restoreIdentity: login => { activeFlushLogin = login; confirmedOwnerLogin = login; }" in dashboard
     assert "window.addEventListener('online', reconnectAfterOnline);" in dashboard
     assert "setTimeout(reconnectOutboxes, 500)" in dashboard
+
+
+def test_dashboard_registers_reconnect_before_offline_startup_can_wait():
+    dashboard = (ROOT / "frontend" / "dashboard.js").read_text()
+
+    listener = dashboard.index("window.addEventListener('online', reconnectAfterOnline);")
+    offline_startup = dashboard.index("await updateOfflineWorkControls();")
+
+    assert listener < offline_startup
diff --git a/tests/test_workspace_bootstrap.py b/tests/test_workspace_bootstrap.py
index 6751822..f13c73f 100644
--- a/tests/test_workspace_bootstrap.py
+++ b/tests/test_workspace_bootstrap.py
@@ -56,6 +56,52 @@ console.log(JSON.stringify({message,status:status.textContent}));
     }
 
 
+def test_workspace_bootstrap_reloads_after_a_failed_offline_load_reconnects():
+    result = run_bootstrap("""
+const status={textContent:''}; const listeners={}; let reloads=0;
+const document={querySelector(selector) {
+  if (selector.startsWith('meta[')) return {content:'feature-workspace-abc.js'};
+  if (selector === '#my-work-action-status') return status;
+  return null;
+}};
+const window={
+  location:{reload(){reloads++;}},
+  addEventListener(name,callback) { listeners[name]=callback; },
+  removeEventListener(name,callback) { if (listeners[name] === callback) delete listeners[name]; },
+};
+const createLoader=()=>({load:async()=>{throw new Error('offline');}});
+try { await loadWorkspace({document,window,createLoader}); } catch (error) {}
+const waiting=Boolean(listeners.online);
+if (listeners.online) listeners.online();
+console.log(JSON.stringify({waiting,reloads,status:status.textContent}));
+""")
+    assert result == {
+        "waiting": True,
+        "reloads": 1,
+        "status": "Workspace could not load. Reconnect to retry automatically, or reload now.",
+    }
+
+
+def test_workspace_bootstrap_reloads_when_reconnect_arrives_before_load_failure():
+    result = run_bootstrap("""
+const status={textContent:''}; const listeners={}; let reloads=0;
+const document={querySelector(selector) {
+  if (selector.startsWith('meta[')) return {content:'feature-workspace-abc.js'};
+  if (selector === '#my-work-action-status') return status;
+  return null;
+}};
+const window={
+  location:{reload(){reloads++;}},
+  addEventListener(name,callback) { listeners[name]=callback; },
+  removeEventListener(name,callback) { if (listeners[name] === callback) delete listeners[name]; },
+};
+const createLoader=()=>({load:async()=>{listeners.online(); throw new Error('offline request');}});
+try { await loadWorkspace({document,window,createLoader}); } catch (error) {}
+console.log(JSON.stringify({reloads,waiting:Boolean(listeners.online)}));
+""")
+    assert result == {"reloads": 1, "waiting": False}
+
+
 def test_workspace_bootstrap_replays_online_event_after_dashboard_registers_handlers():
     result = run_bootstrap("""
 const status={textContent:''}; const listeners={};