diff --git a/.github/scripts/bot-gfi-assign-on-comment.js b/.github/scripts/bot-gfi-assign-on-comment.js
index 80f0bb361..e08462a25 100644
--- a/.github/scripts/bot-gfi-assign-on-comment.js
+++ b/.github/scripts/bot-gfi-assign-on-comment.js
@@ -31,7 +31,9 @@ function commentRequestsAssignment(body) {
  */
 function issueIsGoodFirstIssue(issue) {
     const labels = issue?.labels?.map(label => label.name) ?? [];
-    const isGfi = labels.includes(GOOD_FIRST_ISSUE_LABEL);
+    const isGfi = labels.some(label => 
+        typeof label === 'string' && label.toLowerCase() === GOOD_FIRST_ISSUE_LABEL.toLowerCase()
+    );
 
     console.log('[gfi-assign] issueIsGoodFirstIssue:', {
         labels,
@@ -201,6 +203,25 @@ module.exports = async ({ github, context }) => {
         });
 
         console.log('[gfi-assign] Assignment completed successfully');
+
+        // Chain mentor assignment after successful GFI assignment
+        try {
+            const assignMentor = require('./bot-mentor-assignment.js');
+            await assignMentor({ 
+                github, 
+                context, 
+                assignee: { login: requesterUsername, type: 'User' }  // Pass freshly-assigned username
+            });
+            console.log('[gfi-assign] Mentor assignment chained successfully');
+        } catch (error) {
+            console.error('[gfi-assign] Mentor assignment failed but user assignment succeeded:', {
+                message: error.message,
+                status: error.status,
+                issueNumber: context.payload.issue?.number,
+                assignee: requesterUsername,
+            });
+            // Don't throw error - user assignment was successful
+        }
     } catch (error) {
         console.error('[gfi-assign] Error:', {
             message: error.message,
diff --git a/.github/scripts/bot-mentor-assignment.js b/.github/scripts/bot-mentor-assignment.js
index 8726047a4..358d27954 100644
--- a/.github/scripts/bot-mentor-assignment.js
+++ b/.github/scripts/bot-mentor-assignment.js
@@ -128,10 +128,10 @@ Happy building!
 — Python SDK Team`;
 }
 
-module.exports = async ({ github, context }) => {
+module.exports = async ({ github, context, assignee: passedAssignee }) => {
   try {
     const issue = context.payload.issue;
-    const assignee = context.payload.assignee;
+    const assignee = passedAssignee || context.payload.assignee;
 
     if (!issue?.number || !assignee?.login) {
       return console.log('No issue or assignee found in payload. Skipping.');
diff --git a/.github/workflows/bot-mentor-assignment.yml b/.github/workflows/archive/bot-mentor-assignment.yml
similarity index 100%
rename from .github/workflows/bot-mentor-assignment.yml
rename to .github/workflows/archive/bot-mentor-assignment.yml
diff --git a/CHANGELOG.md b/CHANGELOG.md
index c0347c783..ba30c41ee 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -87,6 +87,7 @@ This changelog is based on [Keep a Changelog](https://keepachangelog.com/en/1.1.
 - Added workflow to prevent assigning intermediate issues to contributors without prior Good First Issue completion (#1143).
 - Added `Client.from_env()` and network-specific factory methods (e.g., `Client.for_testnet()`) to simplify client initialization and reduce boilerplate. [[#1251](https://github.com/hiero-ledger/hiero-sdk-python/issues/1251)]
 - Improved unit test coverage for `TransactionId` class, covering parsing logic, hashing, and scheduled transactions.
+- Chained Good First Issue assignment with mentor assignment to bypass GitHub's anti-recursion protection - mentor assignment now occurs immediately after successful user assignment in the same workflow execution. (#1369)
 
 ### Changed
 - Added global review instructions to CodeRabbit configuration to limit reviews to issue/PR scope and prevent scope creep [#1373]