diff --git a/web/index.html b/web/index.html
index 41abf16..0e3bcc1 100644
--- a/web/index.html
+++ b/web/index.html
@@ -143,6 +143,21 @@
     <input name="to" required spellcheck="false" placeholder="to: alice@example.org or smol://…">
     <input name="subject" spellcheck="false" placeholder="subject">
     <textarea name="body" rows="12" placeholder="message"></textarea>
+    <div id="compose-unpinned" class="seed-card" hidden>
+      <h4>unpinned server</h4>
+      <p class="hint">
+        <strong id="compose-unpinned-host"></strong> is not pinned, and "require a pinned
+        server" refuses to trust a key fetched from it for a new recipient. Fetch its key,
+        compare the fingerprint against what the operator published through a trusted
+        channel, then pin it to send.
+      </p>
+      <div id="compose-unpinned-key-area" hidden></div>
+      <div class="actions">
+        <button type="button" id="compose-unpinned-fetch">Fetch their server's key</button>
+        <button type="button" id="compose-unpinned-pin" class="filled" hidden>Pin and send</button>
+      </div>
+      <span id="compose-unpinned-error" class="error"></span>
+    </div>
     <footer>
       <label class="anon"><input type="checkbox" name="anonymous"> anonymous — omit my address</label>
       <span id="compose-error" class="error"></span>
@@ -211,6 +226,17 @@
       </section>
 
       <section class="panel" data-panel="advanced" hidden>
+        <h3>trust</h3>
+        <label class="check-row">
+          <input type="checkbox" id="require-pinned-server">
+          <span>
+            <span class="check-title">Require a pinned server</span>
+            <span class="hint">Refuse to look up a new recipient's key from a server you haven't
+              pinned. An address that already carries a key, or a recipient you already know, is
+              unaffected — this only applies to a new, hand-typed address.</span>
+          </span>
+        </label>
+
         <h3>rotations</h3>
         <p id="rotations-description" class="hint">Issues a fresh key from your secret with a signed
           certificate proving it replaces this one. Contacts accept the change from that chain, and
diff --git a/web/js/app.js b/web/js/app.js
index 6017a0c..5a5889c 100644
--- a/web/js/app.js
+++ b/web/js/app.js
@@ -736,9 +736,33 @@ function startReply(row) {
   });
 }
 
+// Never silently overwrites a different key already held for the same
+// address — a self-certifying key is still just a claim until compared
+// against what's already trusted. Re-saving an identical key proceeds
+// unasked, matching saveContact()'s own "not a rotation" rule. Throws on
+// decline, so every call site's existing catch already reports it correctly
+// with no further changes needed there.
+async function saveContactChecked(address, keyBytes, verified) {
+  const existing = store.contact(address);
+  if (existing && !timingSafeEqual(existing.key, keyBytes)) {
+    const ok = await confirmDialog({
+      title: `${address} already has a different key`,
+      body: `existing fingerprint: ${fingerprint(existing.key)}\n` +
+            `new fingerprint:      ${fingerprint(keyBytes)}\n\n` +
+            `Overwriting trusts the new key for this address from now on.`,
+      confirmLabel: "use the new key",
+      danger: true,
+    });
+    if (!ok) throw new SmolError(`kept the existing key for ${address}`);
+  }
+  store.saveContact(address, keyBytes, verified);
+}
+
 // Bind a user-supplied address to the key that signed a message. A smol://
 // address carries its own key (verified); a short address is resolved and the
-// result kept on first use. Anything that binds a different key is refused.
+// result kept on first use. A key that disagrees with this message's sender
+// is refused outright; one that disagrees with an address already saved
+// under a different key is asked about instead (saveContactChecked).
 async function nameSender(text, senderKey) {
   const addr = parseAddress(text.trim());
   let key = addr.identity, verified = true;
@@ -753,7 +777,7 @@ async function nameSender(text, senderKey) {
   }
   if (!timingSafeEqual(key, senderKey))
     throw new SmolError("that address carries a different key than this message's sender");
-  store.saveContact(addr.short, senderKey, verified);
+  await saveContactChecked(addr.short, senderKey, verified);
   status(`${addr.short} saved for this sender${verified ? " (verified key)" : ""}`);
   renderFolder();
 }
@@ -783,6 +807,7 @@ function openCompose({ to = "", subject = "", body = "", replyTo = null } = {})
   form.body.value = body;
   form.dataset.replyTo = replyTo ?? "";
   $("compose-error").textContent = "";
+  resetUnpinnedPrompt();
   compose.showModal();
 }
 
@@ -790,24 +815,116 @@ $("write").onclick = () => openCompose();
 
 $("compose-cancel").onclick = () => compose.close();
 
+// Holds the address a refused send is waiting on — "fetch their key, pin it,
+// resend" without losing the draft. Tied to one address at a time: editing
+// the recipient away from it retires the card (the oninput handler below).
+let unpinnedPrompt = null; // { addressShort, host, port, fetchedKey }
+
+function resetUnpinnedPrompt() {
+  unpinnedPrompt = null;
+  $("compose-unpinned").hidden = true;
+  $("compose-unpinned-key-area").hidden = true;
+  $("compose-unpinned-key-area").replaceChildren();
+  $("compose-unpinned-fetch").hidden = false;
+  $("compose-unpinned-pin").hidden = true;
+  $("compose-unpinned-error").textContent = "";
+}
+
+function showUnpinnedPrompt(addr) {
+  // Only #send is disabled mid-flight, not the inputs — if the field no
+  // longer names this address by the time the refusal comes back, there's
+  // nothing to recover for.
+  let live;
+  try { live = parseAddress(compose.querySelector("form").to.value).short; } catch { live = null; }
+  if (live !== addr.short) return;
+  unpinnedPrompt = { addressShort: addr.short, host: addr.host, port: addr.port, fetchedKey: null };
+  $("compose-unpinned-host").textContent = addr.host;
+  $("compose-unpinned").hidden = false;
+}
+
 // Every submission is a send: cancel is a plain button, and Enter in a field
 // submits with no submitter — which the old check read as cancel, discarding
-// the draft.
-compose.querySelector("form").onsubmit = async (event) => {
-  event.preventDefault();
-  const form = event.target;
+// the draft. Factored out from the submit handler so "Pin and send" can
+// retry the exact same attempt inline, rather than synthesizing a submit.
+async function attemptSend(form) {
+  const toText = form.to.value;
   const send = $("send");
   $("compose-error").textContent = "";
   send.disabled = true;  // one click, one envelope: a second seals a second message
   try {
-    await sendMail(form.to.value, form.subject.value, form.body.value, form.dataset.replyTo,
+    await sendMail(toText, form.subject.value, form.body.value, form.dataset.replyTo,
       form.elements.anonymous.checked);
     compose.close();
   } catch (err) {
+    if (err instanceof UnpinnedServerError) {
+      let addr;
+      try { addr = parseAddress(toText); } catch { addr = null; }
+      if (addr) { showUnpinnedPrompt(addr); return; }
+    }
     $("compose-error").textContent = err.message;
+    resetUnpinnedPrompt();
   } finally {
     send.disabled = false;
   }
+}
+
+compose.querySelector("form").onsubmit = (event) => {
+  event.preventDefault();
+  attemptSend(event.target);
+};
+
+compose.querySelector("form").elements.to.oninput = () => {
+  if (!unpinnedPrompt) return;
+  let short;
+  try { short = parseAddress(compose.querySelector("form").to.value).short; } catch { short = null; }
+  if (short !== unpinnedPrompt.addressShort) resetUnpinnedPrompt();
+};
+
+$("compose-unpinned-fetch").onclick = async () => {
+  if (!unpinnedPrompt) return;
+  const { host, port, addressShort } = unpinnedPrompt;
+  const button = $("compose-unpinned-fetch");
+  button.disabled = true;
+  $("compose-unpinned-error").textContent = "";
+  try {
+    // Bypasses connect() deliberately, same reasoning as onboarding's server
+    // screen: its "UNVERIFIED" toast would sit over the button that's about
+    // to pin the result.
+    const timeoutMs = store.timeoutSeconds() * 1000;
+    const stream = await connectStream(host, port, timeoutMs);
+    const opened = await openSession(stream, host, null, timeoutMs);
+    opened.session.stream.close();
+    if (!unpinnedPrompt || unpinnedPrompt.addressShort !== addressShort) return;  // retired mid-fetch
+    unpinnedPrompt.fetchedKey = opened.serverStatic;
+    $("compose-unpinned-key-area").hidden = false;
+    $("compose-unpinned-key-area").replaceChildren(
+      field("fingerprint", fingerprint(opened.serverStatic)),
+      field("key", b32encode(opened.serverStatic)),
+      el("p", { className: "hint", textContent:
+        "Compare this against what the operator published through a trusted channel." }));
+    $("compose-unpinned-fetch").hidden = true;
+    $("compose-unpinned-pin").hidden = false;
+  } catch (err) {
+    $("compose-unpinned-error").textContent = err.message;
+  } finally {
+    button.disabled = false;
+  }
+};
+
+$("compose-unpinned-pin").onclick = async () => {
+  if (!unpinnedPrompt?.fetchedKey) return;
+  const { host, fetchedKey } = unpinnedPrompt;
+  const button = $("compose-unpinned-pin");
+  button.disabled = true;
+  try {
+    store.pinServer(host, fetchedKey);  // a local write, done inline before the retry
+    resetUnpinnedPrompt();
+    await attemptSend(compose.querySelector("form"));
+  } catch (err) {
+    $("compose-unpinned-error").textContent = err.message;
+  } finally {
+    button.disabled = false;
+  }
 };
 
 async function sendMail(toText, subject, body, replyTo, anonymous) {
@@ -848,14 +965,31 @@ async function sendMail(toText, subject, body, replyTo, anonymous) {
   if (folder === "sent") renderFolder();
 }
 
+// Thrown only when the key would be learned from a server the user hasn't
+// pinned: a bare address, not yet a contact, host unpinned. A distinct class,
+// not a SmolError with a particular message, so compose's catch can show the
+// recovery card instead of plain text.
+class UnpinnedServerError extends SmolError {
+  constructor(host) {
+    super(`${host} is not pinned`);
+    this.host = host;
+  }
+}
+
 // Prefer a key we already trust; fall back to RESOLVE with trust on first use.
+// A smol:// address and an already-known contact are exempt from "require a
+// pinned server" below by construction — both return before that check is
+// ever reached, which is what keeps the gate from blocking sends it was
+// never meant to touch.
 async function resolveRecipient(addr) {
   if (addr.identity) {
-    store.saveContact(addr.short, addr.identity, true);
+    await saveContactChecked(addr.short, addr.identity, true);
     return addr.identity;
   }
   const known = store.contact(addr.short);
   if (known) return known.key;
+  if (store.requirePinnedServer() && !store.serverPin(addr.host))
+    throw new UnpinnedServerError(addr.host);
   const opened = await connect(addr, { requirePin: false });
   let current;
   try {
@@ -1062,6 +1196,9 @@ function openContact(address) {
     field("fingerprint", fingerprint(known.key)),
     field("public key", b32encode(known.key)),
     field("address", addr.uri(known.key), false, copyButton(addr.uri(known.key), "address")),
+    field("server", addr.host, false,
+      el("span", { className: store.serverPin(addr.host) ? "badge ok" : "badge",
+        textContent: store.serverPin(addr.host) ? "pinned" : "not pinned" })),
     el("div", { className: "seed-card" },
       el("h4", { textContent: "accept token" }),
       el("p", { className: "hint", textContent: isAccepted
@@ -1200,6 +1337,7 @@ $("settings-open").onclick = () => openSettings();
 $("settings-close").onclick = () => settings.close();
 
 $("leave-on-server").onchange = (event) => store.setLeaveOnServer(event.target.checked);
+$("require-pinned-server").onchange = (event) => store.setRequirePinnedServer(event.target.checked);
 
 // --- settings panels --------------------------------------------------------------
 
@@ -1207,6 +1345,7 @@ $("leave-on-server").onchange = (event) => store.setLeaveOnServer(event.target.c
 // call this rather than reason about which panel it touched.
 function renderSettings() {
   $("leave-on-server").checked = store.leaveOnServer();
+  $("require-pinned-server").checked = store.requirePinnedServer();
   $("backup-error").textContent = "";
   renderIdentityPanel();
   renderServerPanel();
@@ -1312,13 +1451,13 @@ function cleanHost(hostText) {
   return host;
 }
 
-$("import-form").onsubmit = (event) => {
+$("import-form").onsubmit = async (event) => {
   event.preventDefault();
   const form = event.target;
   try {
     const addr = parseAddress(form.uri.value.trim());
     if (!addr.identity) throw new SmolError("import needs a smol:// address carrying a key");
-    store.saveContact(addr.short, addr.identity, true);
+    await saveContactChecked(addr.short, addr.identity, true);
     status(`imported ${addr.short}  ${b32encode(addr.identity)}  (verified)\n` +
       `fingerprint: ${fingerprint(addr.identity)}`);
     renderFolder();
diff --git a/web/js/store.js b/web/js/store.js
index 25d43b9..e2924b8 100644
--- a/web/js/store.js
+++ b/web/js/store.js
@@ -145,6 +145,18 @@ export function allPins() {
   return Object.entries(load().servers || {}).map(([host, key]) => ({ host, key }));
 }
 
+// §4/first contact: when true, resolving a never-before-seen recipient's key
+// from a server that isn't pinned is refused instead of merely toasted after
+// the envelope is already sealed. Persisted, not in-memory — an in-memory
+// toggle fails open on every restart, worth little as a security setting.
+export function requirePinnedServer() {
+  return load().requirePinnedServer ?? false;
+}
+
+export function setRequirePinnedServer(value) {
+  update(state => { state.requirePinnedServer = value; });
+}
+
 // --- FETCH behavior and cursor (§6.1) -------------------------------------------
 
 // When true, fetch does not acknowledge (delete) what it retrieves — mail
diff --git a/web/style.css b/web/style.css
index 485bcd3..8d24a1d 100644
--- a/web/style.css
+++ b/web/style.css
@@ -431,9 +431,14 @@ dialog::backdrop { background: var(--backdrop); }
 .dialog-head .icon-only { color: var(--muted); }
 .dialog-head .icon-only:hover { color: var(--fg); }
 
+/* The recovery card can push content past the viewport on a short window;
+   dialog's own overflow:hidden would just clip it with no way back. */
+#compose { overflow-y: auto; }
 #compose form { display: flex; flex-direction: column; gap: 10px; padding: 20px 22px; }
 #compose input, #compose textarea { width: 100%; }
 #compose textarea { font-family: inherit; resize: vertical; }
+#compose .seed-card { margin: 0; }
+#compose .actions { display: flex; gap: 8px; margin: 4px 0; }
 #compose footer { display: flex; gap: 8px; align-items: center; justify-content: flex-end; padding-top: 4px; flex-wrap: wrap; }
 #compose .anon { font-size: 13px; color: var(--muted); margin-right: auto; display: flex; align-items: center; gap: 6px; white-space: nowrap; }