diff --git a/packages/core/src/config/config.test.ts b/packages/core/src/config/config.test.ts
index 2ccbb4c546..384e97cbb2 100644
--- a/packages/core/src/config/config.test.ts
+++ b/packages/core/src/config/config.test.ts
@@ -2029,7 +2029,7 @@ describe('Config JIT Initialization', () => {
       expect(mockOnReload).toHaveBeenCalled();
       expect(skillManager.setDisabledSkills).toHaveBeenCalledWith(['skill2']);
       expect(toolRegistry.registerTool).toHaveBeenCalled();
-      expect(toolRegistry.unregisterTool).not.toHaveBeenCalledWith(
+      expect(toolRegistry.unregisterTool).toHaveBeenCalledWith(
         ACTIVATE_SKILL_TOOL_NAME,
       );
     });
diff --git a/packages/core/src/config/config.ts b/packages/core/src/config/config.ts
index 4677ef155e..91d16b2b70 100644
--- a/packages/core/src/config/config.ts
+++ b/packages/core/src/config/config.ts
@@ -761,6 +761,7 @@ export class Config {
 
       // Re-register ActivateSkillTool to update its schema with the discovered enabled skill enums
       if (this.getSkillManager().getSkills().length > 0) {
+        this.getToolRegistry().unregisterTool(ActivateSkillTool.Name);
         this.getToolRegistry().registerTool(
           new ActivateSkillTool(this, this.messageBus),
         );
@@ -1568,6 +1569,7 @@ export class Config {
 
     // Re-register ActivateSkillTool to update its schema with the newly discovered skills
     if (this.getSkillManager().getSkills().length > 0) {
+      this.getToolRegistry().unregisterTool(ActivateSkillTool.Name);
       this.getToolRegistry().registerTool(
         new ActivateSkillTool(this, this.messageBus),
       );