diff --git a/apps/web/components/content/documentation-proposals.tsx b/apps/web/components/content/documentation-proposals.tsx
index f163d8a..c84a3c5 100644
--- a/apps/web/components/content/documentation-proposals.tsx
+++ b/apps/web/components/content/documentation-proposals.tsx
@@ -607,7 +607,8 @@ export function DocumentationProposals({
                         {proposal.title}
                       </span>
                       <span className="text-muted-foreground text-xs">
-                        {proposal.captured.length} files ·{" "}
+                        {proposal.captured.length}{" "}
+                        {proposal.captured.length === 1 ? "file" : "files"} ·{" "}
                         {new Date(proposal.createdAt).toLocaleString()}
                       </span>
                     </span>
diff --git a/apps/web/components/content/documentation-source-manage.tsx b/apps/web/components/content/documentation-source-manage.tsx
index 652f190..9fdc373 100644
--- a/apps/web/components/content/documentation-source-manage.tsx
+++ b/apps/web/components/content/documentation-source-manage.tsx
@@ -21,7 +21,10 @@ import {
   SummaryRow,
 } from "@/components/content/documentation-connect-parts";
 import type { DocumentationGitSource } from "@/lib/api";
-import { PagesSourceSection } from "@/components/content/pages-source-section";
+import {
+  DiagnosticList,
+  PagesSourceSection,
+} from "@/components/content/pages-source-section";
 import { ApiReferenceSourceSection } from "@/components/content/api-reference-source-section";
 import { cn } from "@/lib/utils";
 
@@ -84,6 +87,11 @@ type Health = {
   body: string;
 };
 
+/** A sync is underway ("Syncing"); the dialog polls until it settles. */
+export function syncInProgress(source: DocumentationGitSource) {
+  return Boolean(source.binding) && health(source, source.binding!).tone === "info";
+}
+
 function health(source: DocumentationGitSource, binding: Binding): Health {
   if (source.status === "access_lost")
     return {
@@ -103,22 +111,21 @@ function health(source: DocumentationGitSource, binding: Binding): Health {
       title: "Sync paused",
       body: "New commits aren't being picked up. Your site keeps showing the last good version.",
     };
+  const syncing: Health = {
+    tone: "info",
+    title: "Syncing",
+    body: `Checking the newest commit on ${binding.branch}. Your site still shows the previous version.`,
+  };
+  // A new run goes first: retrying after a failure must show (and poll) as syncing.
+  if (source.sync?.status === "queued" || source.sync?.status === "running")
+    return syncing;
   if (source.sync?.status === "failed" || binding.lastDiagnostic)
     return {
       tone: "warning",
       title: "Latest sync didn't go live",
       body: "Your site keeps showing the last good version. Fix the problem in GitHub and sync again.",
     };
-  if (
-    source.sync?.status === "queued" ||
-    source.sync?.status === "running" ||
-    binding.observedSha !== binding.liveSha
-  )
-    return {
-      tone: "info",
-      title: "Syncing",
-      body: `Checking the newest commit on ${binding.branch}. Your site still shows the previous version.`,
-    };
+  if (binding.observedSha !== binding.liveSha) return syncing;
   return {
     tone: "success",
     title: "In sync",
@@ -324,9 +331,13 @@ export function ManageSource({
         onRefresh={onRefresh}
         busy={busy}
       />
-      {(binding.lastDiagnostic || source.sync?.diagnostic) && (
+      {state.tone !== "info" && (binding.lastDiagnostic || source.sync?.diagnostic) && (
         <Callout tone="warning" title="What went wrong">
-          {binding.lastDiagnostic ?? source.sync?.diagnostic}
+          {source.sync?.diagnostics.length ? (
+            <DiagnosticList items={source.sync.diagnostics} />
+          ) : (
+            (binding.lastDiagnostic ?? source.sync?.diagnostic)
+          )}
         </Callout>
       )}
       {binding.lastPrReconcileError && (
diff --git a/apps/web/components/content/documentation-source.tsx b/apps/web/components/content/documentation-source.tsx
index 3374e8d..8faf2b4 100644
--- a/apps/web/components/content/documentation-source.tsx
+++ b/apps/web/components/content/documentation-source.tsx
@@ -6,6 +6,7 @@ import { Check, ExternalLink, Github, GitPullRequest, Loader2 } from "lucide-rea
 import {
   ManageShell,
   ManageSource,
+  syncInProgress,
 } from "@/components/content/documentation-source-manage";
 import { Badge } from "@/components/ui/codelit/badge";
 import { Button } from "@/components/ui/codelit/button";
@@ -555,8 +556,24 @@ export function DocumentationSource({
     verificationAttempt.current = attempt;
     verifyMergedSetup();
   }, [migration?.planId, migration?.status, migration?.pullRequest?.status, setupId]);
+  // While the connected dialog is open, poll: quickly during a sync, and
+  // slowly otherwise so a sync started by a push is noticed too.
+  const watching = open && !wizardMode && source?.binding != null;
+  const pollMs = source && syncInProgress(source) ? 5000 : 30000;
+  useEffect(() => {
+    if (!watching) return;
+    const timer = setInterval(
+      () =>
+        void getDocumentationGitSource()
+          .then(setSource)
+          .catch(() => {}),
+      pollMs,
+    );
+    return () => clearInterval(timer);
+  }, [watching, pollMs]);
   const repoLabel = migration?.repositoryName ?? repositoryName ?? "your repository";
   const fileCount = migration?.total ?? 0;
+  const filesLabel = `${fileCount} ${fileCount === 1 ? "file" : "files"}`;
   const isEmptyRepo = Boolean(migration?.initializeEmptyRepositoryRequired);
   const draftCount = migration?.unpublishedDraftCount ?? 0;
   const noGitHub = !setupId;
@@ -601,7 +618,7 @@ export function DocumentationSource({
         title: "FrontLit checks the files and connects",
         note: "Usually takes a few seconds.",
         state: at[2],
-        waiting: `Checking ${fileCount} files`,
+        waiting: `Checking ${filesLabel}`,
       },
     ];
   };
@@ -1124,7 +1141,7 @@ export function DocumentationSource({
           disabled={busy}
         >
           {isEmptyRepo
-            ? `I approve adding ${migration.selection.directory}/.gitkeep to ${migration.selection.branch} and opening a pull request with these ${fileCount} files.`
+            ? `I approve adding ${migration.selection.directory}/.gitkeep to ${migration.selection.branch} and opening a pull request with ${fileCount === 1 ? "this file" : `these ${filesLabel}`}.`
             : fileCount
               ? `I approve opening a pull request with ${fileCount === 1 ? "this file" : `these ${fileCount} files`}.`
               : `I approve opening a pull request that creates the empty ${migration.selection.directory}/ folder.`}
@@ -1195,7 +1212,7 @@ export function DocumentationSource({
         <StatusBanner>Pull request opened</StatusBanner>
         <StepIntro
           title="Merge it in GitHub to finish"
-          lead={`Review the ${fileCount} files and merge when you're happy. FrontLit picks up the merge on its own, so you can close this window.`}
+          lead={`Review the ${filesLabel} and merge when you're happy. FrontLit picks up the merge on its own, so you can close this window.`}
         />
         <div className="flex items-center gap-3.5 rounded-[0.625rem] border border-border p-4">
           <span className="grid size-10 shrink-0 place-items-center rounded-[0.625rem] bg-[var(--success-soft)] text-[var(--success)]">
@@ -1208,7 +1225,7 @@ export function DocumentationSource({
               {migration.pullRequest?.pullRequestNumber
                 ? ` · #${migration.pullRequest.pullRequestNumber}`
                 : ""}{" "}
-              · {fileCount} files
+              · {filesLabel}
             </span>
           </span>
           {migration.pullRequest?.pullRequestUrl && (
@@ -1417,7 +1434,8 @@ export function DocumentationSource({
                 <Mono>{preflight.directory}/</Mono>
               </SummaryRow>
               <SummaryRow label="Docs" action={null}>
-                {preflight.publishedCount} public of {preflight.fileCount} files
+                {preflight.publishedCount} public of {preflight.fileCount}{" "}
+                {preflight.fileCount === 1 ? "file" : "files"}
               </SummaryRow>
             </>
           ) : (