diff --git a/src/renderer/utils/api/__mocks__/response-mocks.ts b/src/renderer/utils/api/__mocks__/response-mocks.ts
index 714635ab5..6aa43e4a9 100644
--- a/src/renderer/utils/api/__mocks__/response-mocks.ts
+++ b/src/renderer/utils/api/__mocks__/response-mocks.ts
@@ -390,13 +390,13 @@ export const mockDiscussionComments: DiscussionComments = {
   nodes: [
     {
       databaseId: 2258799,
-      createdAt: '2022-02-27T01:22:20Z',
+      createdAt: '2017-02-20T17:51:57Z',
       author: mockDiscussionAuthor,
       replies: {
         nodes: [
           {
             databaseId: 2300902,
-            createdAt: '2022-03-05T17:43:52Z',
+            createdAt: '2017-05-20T17:51:57Z',
             author: mockDiscussionReplier,
           },
         ],
diff --git a/src/renderer/utils/api/client.ts b/src/renderer/utils/api/client.ts
index f6e9d8fc3..70f835f9c 100644
--- a/src/renderer/utils/api/client.ts
+++ b/src/renderer/utils/api/client.ts
@@ -248,8 +248,8 @@ export async function searchDiscussions(
           notification.subject.title,
         ),
         firstDiscussions: 1,
-        lastComments: 1,
-        lastReplies: 1,
+        lastComments: 100,
+        lastReplies: 100,
         firstLabels: 100,
         includeIsAnswered: isAnsweredDiscussionFeatureSupported(
           notification.account,
diff --git a/src/renderer/utils/helpers.ts b/src/renderer/utils/helpers.ts
index be4b47566..c207f3e2e 100644
--- a/src/renderer/utils/helpers.ts
+++ b/src/renderer/utils/helpers.ts
@@ -12,7 +12,7 @@ import type { PlatformType } from './auth/types';
 import { Constants } from './constants';
 import {
   getCheckSuiteAttributes,
-  getLatestDiscussionComment,
+  getClosestDiscussionCommentOrReply,
   getWorkflowRunAttributes,
 } from './subject';
 
@@ -93,10 +93,12 @@ async function getDiscussionUrl(notification: Notification): Promise<Link> {
   if (discussion) {
     url.href = discussion.url;
 
-    const latestComment = getLatestDiscussionComment(discussion.comments.nodes);
-
-    if (latestComment) {
-      url.hash = `#discussioncomment-${latestComment.databaseId}`;
+    const closestComment = getClosestDiscussionCommentOrReply(
+      notification,
+      discussion.comments.nodes,
+    );
+    if (closestComment) {
+      url.hash = `#discussioncomment-${closestComment.databaseId}`;
     }
   }
 
diff --git a/src/renderer/utils/subject.ts b/src/renderer/utils/subject.ts
index c0d4198ac..def607af1 100644
--- a/src/renderer/utils/subject.ts
+++ b/src/renderer/utils/subject.ts
@@ -1,3 +1,5 @@
+import { differenceInMilliseconds } from 'date-fns';
+
 import { logError } from '../../shared/logger';
 import type { Link } from '../types';
 import type {
@@ -162,7 +164,8 @@ async function getGitifySubjectForDiscussion(
     }
   }
 
-  const latestDiscussionComment = getLatestDiscussionComment(
+  const latestDiscussionComment = getClosestDiscussionCommentOrReply(
+    notification,
     discussion.comments.nodes,
   );
 
@@ -190,20 +193,33 @@ async function getGitifySubjectForDiscussion(
   };
 }
 
-export function getLatestDiscussionComment(
+export function getClosestDiscussionCommentOrReply(
+  notification: Notification,
   comments: DiscussionComment[],
 ): DiscussionComment | null {
   if (!comments || comments.length === 0) {
     return null;
   }
 
-  // Return latest reply if available
-  if (comments[0].replies.nodes.length === 1) {
-    return comments[0].replies.nodes[0];
-  }
+  const targetTimestamp = notification.updated_at;
+
+  const allCommentsAndReplies = comments.flatMap((comment) => [
+    comment,
+    ...comment.replies.nodes,
+  ]);
+
+  // Find the closest match using the target timestamp
+  const closestComment = allCommentsAndReplies.reduce((prev, curr) => {
+    const prevDiff = Math.abs(
+      differenceInMilliseconds(prev.createdAt, targetTimestamp),
+    );
+    const currDiff = Math.abs(
+      differenceInMilliseconds(curr.createdAt, targetTimestamp),
+    );
+    return currDiff < prevDiff ? curr : prev;
+  }, allCommentsAndReplies[0]);
 
-  // Return latest comment if no replies
-  return comments[0];
+  return closestComment;
 }
 
 async function getGitifySubjectForIssue(