diff --git a/frontend/openchat-client/src/stores/chat.ts b/frontend/openchat-client/src/stores/chat.ts
index ec00de2e9b..373bd36ec2 100644
--- a/frontend/openchat-client/src/stores/chat.ts
+++ b/frontend/openchat-client/src/stores/chat.ts
@@ -55,6 +55,7 @@ import { draftMessagesStore } from "./draftMessages";
 import { blockedUsers } from "./blockedUsers";
 import { createLsBoolStore } from "./localStorageSetting";
 import { configKeys } from "../utils/config";
+import { recentlySentMessagesStore } from "./recentlySentMessages";
 
 let currentScope: ChatListScope = { kind: "direct_chat" };
 chatListScopeStore.subscribe((s) => (currentScope = s));
@@ -544,6 +545,7 @@ export const threadEvents = derived(
         currentChatBlockedOrSuspendedUsers,
         currentUserIdStore,
         messageFiltersStore,
+        recentlySentMessagesStore,
     ],
     ([
         $serverEvents,
@@ -556,6 +558,7 @@ export const threadEvents = derived(
         $blockedOrSuspendedUsers,
         $currentUserId,
         $messageFilters,
+        $recentlySentMessagesStore,
     ]) => {
         if ($messageContext === undefined || $messageContext.threadRootMessageIndex === undefined)
             return [];
@@ -574,6 +577,7 @@ export const threadEvents = derived(
             $blockedOrSuspendedUsers,
             $currentUserId,
             $messageFilters,
+            $recentlySentMessagesStore,
         );
     },
 );
@@ -728,6 +732,7 @@ export const eventsStore: Readable<EventWrapper<ChatEvent>[]> = derived(
         currentChatBlockedOrSuspendedUsers,
         currentUserIdStore,
         messageFiltersStore,
+        recentlySentMessagesStore,
     ],
     ([
         $serverEventsForSelectedChat,
@@ -740,6 +745,7 @@ export const eventsStore: Readable<EventWrapper<ChatEvent>[]> = derived(
         $blockedOrSuspendedUsers,
         $currentUserId,
         $messageFilters,
+        $recentlySentMessagesStore,
     ]) => {
         const chatId = get(selectedChatId) ?? { kind: "group_chat", groupId: "" };
         const failedForChat = $failedMessages.get({ chatId });
@@ -756,6 +762,7 @@ export const eventsStore: Readable<EventWrapper<ChatEvent>[]> = derived(
             $blockedOrSuspendedUsers,
             $currentUserId,
             $messageFilters,
+            $recentlySentMessagesStore,
         );
     },
 );
diff --git a/frontend/openchat-client/src/stores/mapStore.ts b/frontend/openchat-client/src/stores/mapStore.ts
index eaa5f80fa7..dddc020a37 100644
--- a/frontend/openchat-client/src/stores/mapStore.ts
+++ b/frontend/openchat-client/src/stores/mapStore.ts
@@ -1,10 +1,15 @@
 import type { Writable } from "svelte/store";
-import { get } from "svelte/store";
 
 // eslint-disable-next-line @typescript-eslint/explicit-module-boundary-types
 export function createMapStore<K, V>(store: Writable<Map<K, V>>) {
+    let storeValue = new Map<K, V>();
+    store.subscribe((v) => (storeValue = v));
+
     return {
         subscribe: store.subscribe,
+        get: storeValue.get,
+        has: storeValue.has,
+        size: () => storeValue.size,
         set: store.set,
         insert: (key: K, value: V) => {
             store.update((map) => {
@@ -12,8 +17,11 @@ export function createMapStore<K, V>(store: Writable<Map<K, V>>) {
                 return map;
             });
         },
+        update: (updater: (value: Map<K, V>) => Map<K, V>) => {
+            store.update(updater);
+        },
         delete: (key: K): boolean => {
-            if (get(store).has(key)) {
+            if (storeValue.has(key)) {
                 store.update((map) => {
                     map.delete(key);
                     return map;
diff --git a/frontend/openchat-client/src/stores/recentlySentMessages.ts b/frontend/openchat-client/src/stores/recentlySentMessages.ts
new file mode 100644
index 0000000000..57895f4e08
--- /dev/null
+++ b/frontend/openchat-client/src/stores/recentlySentMessages.ts
@@ -0,0 +1,25 @@
+import { createMapStore } from "./mapStore";
+import { writable } from "svelte/store";
+
+// Key: MessageId, Value: Timestamp
+export const recentlySentMessagesStore = createMapStore<bigint, bigint>(
+    writable(new Map<bigint, bigint>()),
+);
+
+function pruneOldMessages(): void {
+    if (recentlySentMessagesStore.size() > 0) {
+        const oneMinuteAgo = BigInt(Date.now() - 60000);
+        recentlySentMessagesStore.update((map) => {
+            const newMap = new Map<bigint, bigint>();
+            for (const [key, value] of map.entries()) {
+                if (value > oneMinuteAgo) {
+                    newMap.set(key, value);
+                }
+            }
+            return newMap;
+        });
+    }
+}
+
+// Prune old messages every 31 seconds
+window.setInterval(pruneOldMessages, 31000);
diff --git a/frontend/openchat-client/src/stores/unconfirmed.ts b/frontend/openchat-client/src/stores/unconfirmed.ts
index f7f446d672..dabde8db92 100644
--- a/frontend/openchat-client/src/stores/unconfirmed.ts
+++ b/frontend/openchat-client/src/stores/unconfirmed.ts
@@ -6,6 +6,7 @@ import {
     type MessageContext,
     MessageContextMap,
 } from "openchat-shared";
+import { recentlySentMessagesStore } from "./recentlySentMessages";
 
 export type UnconfirmedState = {
     messages: EventWrapper<Message>[];
@@ -81,6 +82,7 @@ function createUnconfirmedStore() {
                 }
                 return state;
             });
+            recentlySentMessagesStore.insert(message.event.messageId, message.timestamp);
         },
         contains: (key: MessageContext, messageId: bigint): boolean => {
             return storeValue.get(key)?.messageIds.has(messageId) ?? false;
diff --git a/frontend/openchat-client/src/utils/chat.ts b/frontend/openchat-client/src/utils/chat.ts
index 5ef20232a6..207a763c07 100644
--- a/frontend/openchat-client/src/utils/chat.ts
+++ b/frontend/openchat-client/src/utils/chat.ts
@@ -896,6 +896,28 @@ function updateReplyContexts(
     }
 }
 
+function createMessageSortFunction(
+    unconfirmed: Set<bigint>,
+    recentlySent: Map<bigint, bigint>,
+): (a: EventWrapper<ChatEvent>, b: EventWrapper<ChatEvent>) => number {
+    return (a: EventWrapper<ChatEvent>, b: EventWrapper<ChatEvent>): number => {
+        // If either message is still unconfirmed, and both were sent recently, use both of their local timestamps,
+        // otherwise we will be comparing the local timestamp of one with the server timestamp of the other
+        if (a.event.kind === "message" && b.event.kind === "message") {
+            if (unconfirmed.has(a.event.messageId) || unconfirmed.has(b.event.messageId)) {
+                const aTimestampOverride = recentlySent.get(a.event.messageId);
+                const bTimestampOverride = recentlySent.get(b.event.messageId);
+
+                if (aTimestampOverride && bTimestampOverride) {
+                    return aTimestampOverride > bTimestampOverride ? 1 : -1;
+                }
+            }
+        }
+
+        return sortByTimestampThenEventIndex(a, b);
+    };
+}
+
 function sortByTimestampThenEventIndex(
     a: EventWrapper<ChatEvent>,
     b: EventWrapper<ChatEvent>,
@@ -1389,6 +1411,7 @@ export function mergeEventsAndLocalUpdates(
     blockedUsers: Set<string>,
     currentUserId: string,
     messageFilters: MessageFilter[],
+    recentlySentMessages: Map<bigint, bigint>,
 ): EventWrapper<ChatEvent>[] {
     const eventIndexes = new DRange();
     eventIndexes.add(expiredEventRanges);
@@ -1466,7 +1489,7 @@ export function mergeEventsAndLocalUpdates(
     if (unconfirmed.length > 0) {
         unconfirmed.sort(sortByTimestampThenEventIndex);
 
-        let anyAdded = false;
+        let unconfirmedAdded = new Set<bigint>();
         for (const message of unconfirmed) {
             // Only include unconfirmed events that are either contiguous with the loaded confirmed events, or are the
             // first events in a new chat
@@ -1478,11 +1501,12 @@ export function mergeEventsAndLocalUpdates(
                         .some((s) => s.low - 1 <= message.index && message.index <= s.high + 1))
             ) {
                 merged.push(processEvent(message));
-                anyAdded = true;
+                unconfirmedAdded.add(message.event.messageId);
             }
         }
-        if (anyAdded) {
-            merged.sort(sortByTimestampThenEventIndex);
+        if (unconfirmedAdded.size > 0) {
+            const sortFn = createMessageSortFunction(unconfirmedAdded, recentlySentMessages);
+            merged.sort(sortFn);
         }
     }