diff --git a/web/e2e-tests/compose.test.ts b/web/e2e-tests/compose.test.ts
index a7a461f50e..02adf09532 100644
--- a/web/e2e-tests/compose.test.ts
+++ b/web/e2e-tests/compose.test.ts
@@ -158,8 +158,8 @@ async function test_send_multirecipient_pm_from_cordelia_pm_narrow(page: Page):
     await pm.click();
     await page.waitForSelector("#compose-textarea", {visible: true});
     const recipient_internal_emails = [
-        await common.get_internal_email_from_name(page, common.fullname.othello),
         await common.get_internal_email_from_name(page, common.fullname.cordelia),
+        await common.get_internal_email_from_name(page, common.fullname.othello),
     ].join(",");
     await common.pm_recipient.expect(page, recipient_internal_emails);
 }
diff --git a/web/e2e-tests/drafts.test.ts b/web/e2e-tests/drafts.test.ts
index aa431e7e29..4f2ee69cd1 100644
--- a/web/e2e-tests/drafts.test.ts
+++ b/web/e2e-tests/drafts.test.ts
@@ -212,7 +212,7 @@ async function test_restore_private_message_draft_via_draft_overlay(page: Page):
         page,
         common.fullname.hamlet,
     );
-    await common.pm_recipient.expect(page, `${hamlet_internal_email},${cordelia_internal_email}`);
+    await common.pm_recipient.expect(page, `${cordelia_internal_email},${hamlet_internal_email}`);
     assert.strictEqual(
         await common.get_text_from_selector(page, "title"),
         "Cordelia, Lear's daughter, King Hamlet - Zulip Dev - Zulip",
diff --git a/web/src/drafts.ts b/web/src/drafts.ts
index 8e2b8a7090..db5d87c25e 100644
--- a/web/src/drafts.ts
+++ b/web/src/drafts.ts
@@ -354,9 +354,10 @@ export function restore_message(draft: LocalStorageDraft): ComposeArguments {
     const recipient_emails = draft.private_message_recipient
         .split(",")
         .filter((email) => people.is_valid_email_for_compose(email));
+    const sorted_recipient_emails = people.sort_emails_by_username(recipient_emails);
     return {
         type: "private",
-        private_message_recipient: recipient_emails.join(","),
+        private_message_recipient: sorted_recipient_emails.join(","),
         content: draft.content,
     };
 }
diff --git a/web/src/message_view.js b/web/src/message_view.js
index ec7d329dc6..f363062848 100644
--- a/web/src/message_view.js
+++ b/web/src/message_view.js
@@ -1211,6 +1211,8 @@ export function narrow_by_recipient(target_id, opts) {
     opts = {then_select_id: target_id, ...opts};
     // don't use message_lists.current as it won't work for muted messages or for out-of-narrow links
     const message = message_store.get(target_id);
+    const emails = message.reply_to.split(",");
+    const reply_to = people.sort_emails_by_username(emails);
 
     switch (message.type) {
         case "private":
@@ -1224,7 +1226,7 @@ export function narrow_by_recipient(target_id, opts) {
                 // in the new view.
                 unread_ops.notify_server_message_read(message);
             }
-            show([{operator: "dm", operand: message.reply_to}], opts);
+            show([{operator: "dm", operand: reply_to.join(",")}], opts);
             break;
 
         case "stream":
diff --git a/web/src/people.ts b/web/src/people.ts
index 5740aac56c..1235205adf 100644
--- a/web/src/people.ts
+++ b/web/src/people.ts
@@ -179,6 +179,24 @@ export function update_email(user_id: number, new_email: string): void {
     // still work correctly.
 }
 
+// A function that sorts Email according to the user's full name
+export function sort_emails_by_username(emails: string[]): (string | undefined)[] {
+    const user_ids = emails.map((email) => get_user_id(email));
+    const name_email_dict = user_ids.map((user_id, index) => ({
+        name:
+            user_id !== undefined && people_by_user_id_dict.has(user_id)
+                ? people_by_user_id_dict.get(user_id)?.full_name
+                : "?",
+        email: emails[index],
+    }));
+
+    const sorted_emails = name_email_dict
+        .sort((a, b) => util.strcmp(a.name!, b.name!))
+        .map(({email}) => email);
+
+    return sorted_emails;
+}
+
 export function get_visible_email(user: User): string {
     if (user.delivery_email) {
         return user.delivery_email;
@@ -268,9 +286,7 @@ export function user_ids_string_to_emails_string(user_ids_string: string): strin
 
     emails = emails.map((email) => email.toLowerCase());
 
-    emails.sort();
-
-    return emails.join(",");
+    return sort_emails_by_username(emails).join(",");
 }
 
 export function user_ids_string_to_ids_array(user_ids_string: string): number[] {
@@ -465,9 +481,7 @@ export function pm_reply_to(message: Message): string | undefined {
         return person.email;
     });
 
-    emails.sort();
-
-    const reply_to = emails.join(",");
+    const reply_to = sort_emails_by_username(emails).join(",");
 
     return reply_to;
 }
diff --git a/web/tests/people.test.js b/web/tests/people.test.js
index 5f95d02914..b1a9635950 100644
--- a/web/tests/people.test.js
+++ b/web/tests/people.test.js
@@ -920,7 +920,7 @@ test_people("message_methods", () => {
     };
     assert.equal(people.pm_with_url(message), "#narrow/dm/301,302-group");
     assert.equal(people.pm_perma_link(message), "#narrow/dm/30,301,302-group");
-    assert.equal(people.pm_reply_to(message), "Athens@example.com,charles@example.com");
+    assert.equal(people.pm_reply_to(message), "charles@example.com,Athens@example.com");
     assert.equal(people.small_avatar_url(message), "http://charles.com/foo.png");
 
     message = {
diff --git a/web/tests/people_errors.test.js b/web/tests/people_errors.test.js
index 4416e34af5..e78e649648 100644
--- a/web/tests/people_errors.test.js
+++ b/web/tests/people_errors.test.js
@@ -48,7 +48,7 @@ run_test("blueslip", () => {
     blueslip.expect("error", "Unknown user_id");
     people.get_actual_name_from_user_id(9999);
 
-    blueslip.expect("error", "Unknown email for get_user_id");
+    blueslip.expect("error", "Unknown email for get_user_id", 2);
     people.get_user_id(unknown_email);
 
     blueslip.expect("warn", "No user_id provided");