diff --git a/src/routes/hooks/poll-imap.ts b/src/routes/hooks/poll-imap.ts
index fbbde7f..ce15c03 100644
--- a/src/routes/hooks/poll-imap.ts
+++ b/src/routes/hooks/poll-imap.ts
@@ -8,6 +8,10 @@ import { simpleParser } from "mailparser";
 import { matchAndUpdateEmails } from "@/lib/email-matching.server";
 
 const MAX_MESSAGES_PER_RUN = 50;
+// Cloudflare Workers drop long-lived TLS sockets when streaming very large
+// IMAP FETCH responses. Skip oversize messages (>5 MB) so a single huge
+// email doesn't kill the whole poll. They can be retrieved manually later.
+const MAX_MESSAGE_SIZE_BYTES = 5 * 1024 * 1024;
 
 export const Route = createFileRoute("/hooks/poll-imap")({
   server: {
@@ -51,13 +55,48 @@ export const Route = createFileRoute("/hooks/poll-imap")({
               const sinceUid = (settings.last_uid ?? 0) + 1;
               const range = `${sinceUid}:*`;
 
-              for await (const msg of client.fetch(
+              // First pass: fetch lightweight envelopes only to learn the
+              // size of each message. Then fetch full source one-by-one,
+              // skipping anything over the size cap.
+              const candidates: Array<{ uid: number; size: number }> = [];
+              for await (const meta of client.fetch(
                 range,
-                { uid: true, source: true, envelope: true, size: true },
+                { uid: true, size: true },
                 { uid: true },
               )) {
+                if (meta.uid <= (settings.last_uid ?? 0)) continue;
+                candidates.push({ uid: meta.uid, size: meta.size ?? 0 });
+                if (candidates.length >= MAX_MESSAGES_PER_RUN * 4) break;
+              }
+
+              for (const cand of candidates) {
                 if (imported >= MAX_MESSAGES_PER_RUN) break;
-                if (msg.uid <= (settings.last_uid ?? 0)) continue;
+
+                // Always advance highestUid so we don't re-attempt skipped messages.
+                if (cand.uid > highestUid) highestUid = cand.uid;
+
+                if (cand.size > MAX_MESSAGE_SIZE_BYTES) {
+                  console.warn(
+                    `Skipping IMAP uid ${cand.uid} (${cand.size} bytes > ${MAX_MESSAGE_SIZE_BYTES})`,
+                  );
+                  continue;
+                }
+
+                let msg: { uid: number; source: Buffer; size?: number } | null = null;
+                try {
+                  for await (const m of client.fetch(
+                    String(cand.uid),
+                    { uid: true, source: true, size: true },
+                    { uid: true },
+                  )) {
+                    msg = m as any;
+                    break;
+                  }
+                } catch (e) {
+                  console.error("Per-message fetch failed uid", cand.uid, e);
+                  continue;
+                }
+                if (!msg) continue;
 
                 let parsed;
                 try {