diff --git a/README.md b/README.md
index de8925b..048ac57 100644
--- a/README.md
+++ b/README.md
@@ -27,7 +27,7 @@ For a server on a non-default port, start the bridge with `uv run bridge.py --al
 - **Identity** (§2): one 32-byte seed; create or restore; the X25519 agreement keys are derived from the Ed25519 keypair. The seed lives in localStorage, mail stays sealed in IndexedDB — the browser profile is the trust boundary.
 - **Addressing** (§3): short `user@host` and self-certifying `smol://` addresses, base32 fingerprints.
 - **Trust** (§4, §8): server keys pinned on first trust, mismatch aborts the handshake; `RESOLVE` over an unpinned session is marked unverified; registration and fetching require a pinned server.
-- **Mail** (§5): sealed and signed envelopes, 1 KiB padding, frontmatter bodies, sent copies sealed to self, fetch verifies id and signature before acknowledging — anything unreadable stays on the server.
+- **Mail** (§5): sealed and signed envelopes, 1 KiB padding, frontmatter bodies, sent copies sealed to self, fetch verifies id and signature before acknowledging — anything unreadable stays on the server. Outgoing mail carries a signed `Reply-To` frontmatter field with the sender's full `smol://` address (an "anonymous" checkbox omits it), so a first-time recipient can name the sender and answer; on receipt such a claim binds only when its key matches the message's signer, and never over an address already pinned to a different key.
 - **Rotation** (§7): rotate with a signed certificate; contacts accept the change from the chain; superseded seeds are kept, since mail sealed to them is readable with nothing else; key changes without a chain are surfaced, never applied silently.
 
 ## Layout
diff --git a/test/client.mjs b/test/client.mjs
index 890b9b0..c443a91 100644
--- a/test/client.mjs
+++ b/test/client.mjs
@@ -201,6 +201,9 @@ const commands = {
 
     const fields = [["Subject", parseOption("--subject")], ["In-Reply-To", parseOption("--reply-to")]]
       .filter(([, v]) => v);
+    if (state.account && !rest.includes("--anonymous"))
+      fields.push(["Reply-To", proto.parseAddress(`${state.account.user}@${state.account.host}` +
+        (state.account.port === proto.DEFAULT_PORT ? "" : `:${state.account.port}`)).uri(me.publicKey)]);
     const body = utf8Bytes(proto.buildFrontmatter(fields, (parseOption("--body") || "") + "\n"));
     const envelope = proto.seal(me, recipient, body);
     const opened = await open(addr.host, addr.port, { requirePin: false });
diff --git a/test/e2e.py b/test/e2e.py
index ca2e7ff..f6000b7 100644
--- a/test/e2e.py
+++ b/test/e2e.py
@@ -107,6 +107,10 @@ def main() -> int:
         alice_read = run(alice + ["read", reply_id[:8]])
         check("alice reads bob's reply", "hello alice" in alice_read, alice_read)
         check("reference client verifies the JS signature", "signature verified" in alice_read)
+        # bob's reply carries his signed smol:// address; a receiver that does
+        # not know the field must still preserve and display it (SPEC.md §5.5)
+        check("reference client preserves the signed reply address",
+              "reply-to:smol://bob@" in alice_read, alice_read)
 
         # --- rotation: the JS client rotates, the reference client walks the chain
         bob_rotated = run(bob + ["rotate"])
diff --git a/web/index.html b/web/index.html
index 43cc861..5367686 100644
--- a/web/index.html
+++ b/web/index.html
@@ -44,6 +44,7 @@
     <label>subject <input name="subject" spellcheck="false"></label>
     <textarea name="body" rows="12"></textarea>
     <footer>
+      <label class="anon"><input type="checkbox" name="anonymous"> anonymous — omit my address</label>
       <span id="compose-error" class="error"></span>
       <button value="cancel">cancel</button>
       <button id="send" value="send">send</button>
diff --git a/web/js/app.js b/web/js/app.js
index 88a5cc1..9024ce3 100644
--- a/web/js/app.js
+++ b/web/js/app.js
@@ -133,18 +133,30 @@ async function renderFolder() {
 // Open an envelope and split its body; anything unreadable shows as such
 // rather than throwing, so one bad message cannot blank the list. The wire
 // carries no sender name, so an unknown key can only be shown as its
-// fingerprint until the user imports the sender's smol:// address.
+// fingerprint until the user binds it to an address — which a signed Reply-To
+// field lets the sender do in-band.
 function describe(row) {
   try {
     const opened = unseal(store.identities(), row.envelope);
     const { fields, body } = parseFrontmatter(new TextDecoder().decode(opened.body));
     const known = store.addressForKey(opened.sender);
+    let replyAddress = null;
+    if (fields["Reply-To"]) {
+      try {
+        const claimed = parseAddress(fields["Reply-To"]);
+        // Only a full smol:// address whose key matches the signer counts;
+        // anything else is ordinary text.
+        if (claimed.identity && timingSafeEqual(claimed.identity, opened.sender))
+          replyAddress = claimed;
+      } catch { /* malformed claim: display, never bind */ }
+    }
     return {
       ...opened,
       fields, body,
       subject: fields.Subject || "",
       from: known ?? `unknown · ${fingerprint(opened.sender)}`,
       knownSender: Boolean(known),
+      replyAddress,
     };
   } catch (err) {
     return { error: err.message };
@@ -177,6 +189,29 @@ async function openMessage(id) {
   if (folder === "inbox") {
     if (opened.knownSender) {
       view.append(replyButton(opened, row));
+    } else if (opened.replyAddress) {
+      // The sender signed their own smol:// address into the payload, so
+      // binding it is one click. A pinned conflicting key is refused (§8).
+      const note = document.createElement("p");
+      note.className = "placeholder";
+      note.textContent =
+        `this message carries the sender's signed address: ${opened.replyAddress.short}`;
+      const save = document.createElement("button");
+      save.textContent = "save sender & reply";
+      save.onclick = () => {
+        try {
+          saveReplyAddress(opened.replyAddress, opened.sender);
+          openMessage(row.id);
+          openCompose({
+            to: opened.replyAddress.short,
+            subject: opened.subject ? (opened.subject.startsWith("Re:") ? opened.subject : `Re: ${opened.subject}`) : "",
+            replyTo: row.id,
+          });
+        } catch (err) {
+          status(err.message, true);
+        }
+      };
+      view.append(note, save);
     } else {
       // The wire gives only a signed key; a reply needs the sender's address,
       // which the user supplies once and we bind to that exact key.
@@ -247,6 +282,19 @@ async function nameSender(text, senderKey) {
   renderFolder();
 }
 
+// A signed Reply-To is the sender's own claim, so it saves as verified — but
+// never over an address already pinned to a different key (§8: a key change
+// without a rotation chain needs out-of-band confirmation).
+function saveReplyAddress(addr, senderKey) {
+  const existing = store.contact(addr.short);
+  if (existing && !timingSafeEqual(existing.key, senderKey))
+    throw new SmolError(`${addr.short} is already known with a different key — ` +
+      `verify out of band before replying`);
+  store.saveContact(addr.short, senderKey, true);
+  status(`${addr.short} saved for this sender (verified key)`);
+  renderFolder();
+}
+
 // --- compose and send -----------------------------------------------------------
 
 const compose = $("compose");
@@ -272,20 +320,26 @@ compose.querySelector("form").onsubmit = async (event) => {
   const form = event.target;
   $("compose-error").textContent = "";
   try {
-    await sendMail(form.to.value, form.subject.value, form.body.value, form.dataset.replyTo);
+    await sendMail(form.to.value, form.subject.value, form.body.value, form.dataset.replyTo,
+      form.elements.anonymous.checked);
     compose.close();
   } catch (err) {
     $("compose-error").textContent = err.message;
   }
 };
 
-async function sendMail(toText, subject, body, replyTo) {
+async function sendMail(toText, subject, body, replyTo, anonymous) {
   const me = store.identity();
   if (!me) throw new SmolError("no identity yet");
   const addr = parseAddress(toText);
   const recipient = await resolveRecipient(addr);
-  const fields = [["Subject", subject], ["In-Reply-To", replyTo]].filter(([, v]) => v);
-  const bodyBytes = utf8Bytes(buildFrontmatter(fields, body.replace(/\s+$/, "") + "\n"));
+  const account = accountAddress();
+  const fields = [["Subject", subject], ["In-Reply-To", replyTo]];
+  // A signed Reply-To lets a first-time recipient name and answer us (§5.5
+  // allows unknown keys); "anonymous" omits it.
+  if (account && !anonymous) fields.push(["Reply-To", account.uri(me.publicKey)]);
+  const bodyBytes = utf8Bytes(buildFrontmatter(fields.filter(([, v]) => v),
+    body.replace(/\s+$/, "") + "\n"));
   const envelope = seal(me, recipient, bodyBytes);
   const opened = await connect(addr, { requirePin: false });
   try {
diff --git a/web/style.css b/web/style.css
index 58756de..5918f67 100644
--- a/web/style.css
+++ b/web/style.css
@@ -118,6 +118,7 @@ dialog::backdrop { background: rgba(0, 0, 0, 0.25); }
 #compose input { flex: 1; }
 #compose textarea { font-family: inherit; }
 #compose footer { display: flex; gap: 8px; justify-content: flex-end; align-items: center; }
+#compose .anon { font-size: 12px; color: var(--muted); display: flex; align-items: center; gap: 6px; }
 .error { color: var(--warn); font-size: 13px; margin-right: auto; }
 
 #settings section { margin-bottom: 20px; }