diff --git a/web/src/narrow_banner.ts b/web/src/narrow_banner.ts
index 3ff5c12b0b..9405fcc632 100644
--- a/web/src/narrow_banner.ts
+++ b/web/src/narrow_banner.ts
@@ -346,12 +346,23 @@ export function pick_empty_narrow_banner(): NarrowBannerData {
                         }),
                     };
                 }
+                // If the recipient is deactivated, we cannot start the conversation.
+                if (!people.is_person_active(recipient_user.user_id)) {
+                    return {
+                        title: $t(
+                            {
+                                defaultMessage: "You have no direct messages with {person}.",
+                            },
+                            {person: recipient_user.full_name},
+                        ),
+                    };
+                }
                 return {
                     title: $t(
                         {
                             defaultMessage: "You have no direct messages with {person} yet.",
                         },
-                        {person: people.get_by_user_id(user_ids[0]).full_name},
+                        {person: recipient_user.full_name},
                     ),
                     html: $t_html(
                         {
@@ -366,6 +377,11 @@ export function pick_empty_narrow_banner(): NarrowBannerData {
                     ),
                 };
             }
+            if (people.get_non_active_user_ids_count(user_ids) !== 0) {
+                return {
+                    title: $t({defaultMessage: "You have no direct messages with these users."}),
+                };
+            }
             return {
                 title: $t({defaultMessage: "You have no direct messages with these users yet."}),
                 html: $t_html(
diff --git a/web/src/people.ts b/web/src/people.ts
index 1235205adf..37fcdb1dbe 100644
--- a/web/src/people.ts
+++ b/web/src/people.ts
@@ -1034,6 +1034,16 @@ export function get_non_active_human_ids(): number[] {
     return human_ids;
 }
 
+export function get_non_active_user_ids_count(user_ids: number[]): number {
+    let count = 0;
+    for (const user_id of user_ids) {
+        if (non_active_user_dict.has(user_id)) {
+            count += 1;
+        }
+    }
+    return count;
+}
+
 export function get_bot_ids(): number[] {
     const bot_ids = [];
 
diff --git a/web/tests/message_view.test.js b/web/tests/message_view.test.js
index d3ac434fb6..6311bd4e1f 100644
--- a/web/tests/message_view.test.js
+++ b/web/tests/message_view.test.js
@@ -418,6 +418,17 @@ run_test("show_empty_narrow_message", ({mock_template}) => {
         ),
     );
 
+    // sending direct messages to deactivated user
+    realm.realm_direct_message_permission_group = everyone.id;
+    people.deactivate(alice);
+    set_filter([["dm", alice.email]]);
+    narrow_banner.show_empty_narrow_message();
+    assert.equal(
+        $(".empty_feed_notice_main").html(),
+        empty_narrow_html("translated: You have no direct messages with Alice Smith."),
+    );
+    people.add_active_user(alice);
+
     people.add_active_user(me);
     people.initialize_current_user(me.user_id);
     set_filter([["dm", me.email]]);
@@ -440,6 +451,16 @@ run_test("show_empty_narrow_message", ({mock_template}) => {
         ),
     );
 
+    // group dm with a deactivated user
+    people.deactivate(alice);
+    set_filter([["dm", ray.email + "," + alice.email]]);
+    narrow_banner.show_empty_narrow_message();
+    assert.equal(
+        $(".empty_feed_notice_main").html(),
+        empty_narrow_html("translated: You have no direct messages with these users."),
+    );
+    people.add_active_user(alice);
+
     // organization has disabled sending direct messages
     realm.realm_direct_message_permission_group = nobody.id;
 
diff --git a/web/tests/people.test.js b/web/tests/people.test.js
index b1a9635950..d86544eb8d 100644
--- a/web/tests/people.test.js
+++ b/web/tests/people.test.js
@@ -335,6 +335,7 @@ test_people("basics", ({override}) => {
     // Now deactivate isaac
     people.deactivate(isaac);
     assert.equal(people.get_non_active_human_ids().length, 1);
+    assert.equal(people.get_non_active_user_ids_count([isaac.user_id]), 1);
     assert.equal(people.get_active_human_count(), 1);
     assert.equal(people.is_active_user_for_popover(isaac.user_id), false);
     assert.equal(people.is_valid_email_for_compose(isaac.email), true);