diff --git a/packages/ai-chat-ui/src/browser/ai-chat-ui-contribution.ts b/packages/ai-chat-ui/src/browser/ai-chat-ui-contribution.ts
index 053c5f0a4dc29..9e440b112c8f2 100644
--- a/packages/ai-chat-ui/src/browser/ai-chat-ui-contribution.ts
+++ b/packages/ai-chat-ui/src/browser/ai-chat-ui-contribution.ts
@@ -17,8 +17,8 @@
 import { inject, injectable } from '@theia/core/shared/inversify';
 import { CommandRegistry, QuickInputButton, QuickInputService, QuickPickItem } from '@theia/core';
 import { Widget } from '@theia/core/lib/browser';
-import { AI_CHAT_NEW_CHAT_WINDOW_COMMAND, AI_CHAT_SHOW_CHATS_COMMAND, ChatCommands } from './chat-view-commands';
-import { ChatAgentLocation, ChatService } from '@theia/ai-chat';
+import { AI_CHAT_NEW_CHAT_WINDOW_COMMAND, AI_CHAT_NEW_CHAT_WINDOW_WITH_PINNED_AGENT_COMMAND, AI_CHAT_SHOW_CHATS_COMMAND, ChatCommands } from './chat-view-commands';
+import { ChatAgent, ChatAgentLocation, ChatService } from '@theia/ai-chat';
 import { AbstractViewContribution } from '@theia/core/lib/browser/shell/view-contribution';
 import { TabBarToolbarContribution, TabBarToolbarRegistry } from '@theia/core/lib/browser/shell/tab-bar-toolbar';
 import { ChatViewWidget } from './chat-view-widget';
@@ -79,6 +79,12 @@ export class AIChatContribution extends AbstractViewContribution<ChatViewWidget>
             isEnabled: widget => this.withWidget(widget, () => true),
             isVisible: widget => this.withWidget(widget, () => true),
         });
+        registry.registerCommand(AI_CHAT_NEW_CHAT_WINDOW_WITH_PINNED_AGENT_COMMAND, {
+            // TODO - not working if function arg is set to type ChatAgent | undefined ?
+            execute: (...args: unknown[]) => this.chatService.createSession(ChatAgentLocation.Panel, {focus: true}, args[1] as ChatAgent | undefined),
+            isEnabled: widget => this.withWidget(widget, () => true),
+            isVisible: widget => this.withWidget(widget, () => true),
+        });
         registry.registerCommand(AI_CHAT_SHOW_CHATS_COMMAND, {
             execute: () => this.selectChat(),
             isEnabled: widget => this.withWidget(widget, () => true) && this.chatService.getSessions().length > 1,
diff --git a/packages/ai-chat-ui/src/browser/chat-input-widget.tsx b/packages/ai-chat-ui/src/browser/chat-input-widget.tsx
index 12f2cd102eb0a..f549758ec4d83 100644
--- a/packages/ai-chat-ui/src/browser/chat-input-widget.tsx
+++ b/packages/ai-chat-ui/src/browser/chat-input-widget.tsx
@@ -25,6 +25,7 @@ import { IMouseEvent } from '@theia/monaco-editor-core';
 import { Deferred } from '@theia/core/lib/common/promise-util';
 
 type Query = (query: string) => Promise<void>;
+type Unpin = () => void;
 type Cancel = (requestModel: ChatRequestModel) => void;
 
 @injectable()
@@ -53,6 +54,10 @@ export class AIChatInputWidget extends ReactWidget {
     set onQuery(query: Query) {
         this._onQuery = query;
     }
+    private _onUnpin: Unpin;
+    set onUnpin(unpin: Unpin) {
+        this._onUnpin = unpin;
+    }
     private _onCancel: Cancel;
     set onCancel(cancel: Cancel) {
         this._onCancel = cancel;
@@ -62,6 +67,11 @@ export class AIChatInputWidget extends ReactWidget {
         this._chatModel = chatModel;
         this.update();
     }
+    private _pinnedAgent: ChatAgent | undefined;
+    set pinnedAgent(pinnedAgent: ChatAgent | undefined) {
+        this._pinnedAgent = pinnedAgent;
+        this.update();
+    }
 
     @postConstruct()
     protected init(): void {
@@ -87,8 +97,10 @@ export class AIChatInputWidget extends ReactWidget {
         return (
             <ChatInput
                 onQuery={this._onQuery.bind(this)}
+                onUnpin={this._onUnpin.bind(this)}
                 onCancel={this._onCancel.bind(this)}
                 chatModel={this._chatModel}
+                pinnedAgent={this._pinnedAgent}
                 getChatAgents={this.getChatAgents.bind(this)}
                 editorProvider={this.editorProvider}
                 untitledResourceResolver={this.untitledResourceResolver}
@@ -120,8 +132,10 @@ export class AIChatInputWidget extends ReactWidget {
 interface ChatInputProperties {
     onCancel: (requestModel: ChatRequestModel) => void;
     onQuery: (query: string) => void;
+    onUnpin: () => void;
     isEnabled?: boolean;
     chatModel: ChatModel;
+    pinnedAgent?: ChatAgent;
     getChatAgents: () => ChatAgent[];
     editorProvider: MonacoEditorProvider;
     untitledResourceResolver: UntitledResourceResolver;
@@ -267,9 +281,19 @@ const ChatInput: React.FunctionComponent<ChatInputProperties> = (props: ChatInpu
             placeholderRef.current?.classList.add('hidden');
         }
     };
+    
+    const handleUnpin = () => {
+        props.onUnpin();
+    };
 
     return <div className='theia-ChatInput'>
         <div className='theia-ChatInput-Editor-Box'>
+            {props.pinnedAgent !== undefined &&
+                <div className='theia-ChatInput-Popup'>
+                    <span>@{props.pinnedAgent.name}</span>
+                    <span className="codicon codicon-remove-close option" title="unpin" onClick={handleUnpin} />
+                </div>
+            }
             <div className='theia-ChatInput-Editor' ref={editorContainerRef} onKeyDown={onKeyDown} onFocus={handleInputFocus} onBlur={handleInputBlur}>
                 <div ref={placeholderRef} className='theia-ChatInput-Editor-Placeholder'>Ask a question</div>
             </div>
diff --git a/packages/ai-chat-ui/src/browser/chat-view-commands.ts b/packages/ai-chat-ui/src/browser/chat-view-commands.ts
index f513e32690444..082c819dff22e 100644
--- a/packages/ai-chat-ui/src/browser/chat-view-commands.ts
+++ b/packages/ai-chat-ui/src/browser/chat-view-commands.ts
@@ -39,6 +39,11 @@ export const AI_CHAT_NEW_CHAT_WINDOW_COMMAND: Command = {
     iconClass: codicon('add')
 };
 
+export const AI_CHAT_NEW_CHAT_WINDOW_WITH_PINNED_AGENT_COMMAND: Command = {
+    id: 'ai-chat-ui.new-chat-with-pinned-agent',
+    iconClass: codicon('add')
+};
+
 export const AI_CHAT_SHOW_CHATS_COMMAND: Command = {
     id: 'ai-chat-ui.show-chats',
     iconClass: codicon('history')
diff --git a/packages/ai-chat-ui/src/browser/chat-view-widget.tsx b/packages/ai-chat-ui/src/browser/chat-view-widget.tsx
index 3793d0f6c7f4a..367722b2af650 100644
--- a/packages/ai-chat-ui/src/browser/chat-view-widget.tsx
+++ b/packages/ai-chat-ui/src/browser/chat-view-widget.tsx
@@ -91,8 +91,10 @@ export class ChatViewWidget extends BaseWidget implements ExtractableWidget, Sta
         this.chatSession = this.chatService.createSession();
 
         this.inputWidget.onQuery = this.onQuery.bind(this);
+        this.inputWidget.onUnpin = this.onUnpin.bind(this);
         this.inputWidget.onCancel = this.onCancel.bind(this);
         this.inputWidget.chatModel = this.chatSession.model;
+        this.inputWidget.pinnedAgent = this.chatSession.pinnedAgent;
         this.treeWidget.trackChatModel(this.chatSession.model);
 
         this.initListeners();
@@ -111,10 +113,12 @@ export class ChatViewWidget extends BaseWidget implements ExtractableWidget, Sta
         this.toDispose.push(
             this.chatService.onActiveSessionChanged(event => {
                 const session = event.sessionId ? this.chatService.getSession(event.sessionId) : this.chatService.createSession();
+
                 if (session) {
                     this.chatSession = session;
                     this.treeWidget.trackChatModel(this.chatSession.model);
                     this.inputWidget.chatModel = this.chatSession.model;
+                    this.inputWidget.pinnedAgent = this.chatSession.pinnedAgent;
                     if (event.focus) {
                         this.show();
                     }
@@ -167,6 +171,8 @@ export class ChatViewWidget extends BaseWidget implements ExtractableWidget, Sta
             if (responseModel.isError) {
                 this.messageService.error(responseModel.errorObject?.message ?? 'An error occurred druring chat service invocation.');
             }
+        }).finally(() => {
+            this.inputWidget.pinnedAgent = this.chatSession.pinnedAgent;
         });
         if (!requestProgress) {
             this.messageService.error(`Was not able to send request "${chatRequest.text}" to session ${this.chatSession.id}`);
@@ -175,6 +181,11 @@ export class ChatViewWidget extends BaseWidget implements ExtractableWidget, Sta
         // Tree Widget currently tracks the ChatModel itself. Therefore no notification necessary.
     }
 
+    protected onUnpin(): void {
+        this.chatSession.pinnedAgent = undefined;
+        this.inputWidget.pinnedAgent = this.chatSession.pinnedAgent;
+    }
+
     protected onCancel(requestModel: ChatRequestModel): void {
         // TODO we should pass a cancellation token with the request (or retrieve one from the request invocation) so we can cleanly cancel here
         // For now we cancel manually via casting
diff --git a/packages/ai-chat-ui/src/browser/style/index.css b/packages/ai-chat-ui/src/browser/style/index.css
index faf9ada7849e9..b4c07a1c0e72d 100644
--- a/packages/ai-chat-ui/src/browser/style/index.css
+++ b/packages/ai-chat-ui/src/browser/style/index.css
@@ -7,8 +7,8 @@
   flex: 1;
 }
 
-.chat-input-widget > .ps__rail-x,
-.chat-input-widget > .ps__rail-y {
+.chat-input-widget>.ps__rail-x,
+.chat-input-widget>.ps__rail-y {
   display: none !important;
 }
 
@@ -23,7 +23,7 @@
   overflow-wrap: break-word;
 }
 
-div:last-child > .theia-ChatNode {
+div:last-child>.theia-ChatNode {
   border: none;
 }
 
@@ -59,6 +59,7 @@ div:last-child > .theia-ChatNode {
 }
 
 @keyframes dots {
+
   0%,
   20% {
     content: "";
@@ -95,15 +96,18 @@ div:last-child > .theia-ChatNode {
   margin-left: auto;
   line-height: 18px;
 }
+
 .theia-ChatNodeToolbar .theia-ChatNodeToolbarAction {
   display: none;
   align-items: center;
   padding: 4px;
   border-radius: 5px;
 }
+
 .theia-ChatNode:hover .theia-ChatNodeToolbar .theia-ChatNodeToolbarAction {
   display: inline-block;
 }
+
 .theia-ChatNodeToolbar .theia-ChatNodeToolbarAction:hover {
   cursor: pointer;
   background-color: var(--theia-toolbar-hoverBackground);
@@ -118,7 +122,7 @@ div:last-child > .theia-ChatNode {
   padding-inline-start: 1rem;
 }
 
-.theia-ChatNode li > p {
+.theia-ChatNode li>p {
   margin-top: 0;
   margin-bottom: 0;
 }
@@ -169,11 +173,29 @@ div:last-child > .theia-ChatNode {
   overflow: hidden;
 }
 
+.theia-ChatInput-Popup {
+  position: relative;
+  bottom: -5px;
+  right: -2px;
+  padding-top: 9px;
+  padding-left: 10px;
+  padding-right: 10px;
+  padding-bottom: 11px;
+  display: flex;
+  flex-direction: row;
+  align-items: start;
+  align-self: flex-end;
+  gap: 10px;
+  border: var(--theia-border-width) solid var(--theia-dropdown-border);
+  border-radius: 4px;
+}
+
 .theia-ChatInput-Editor {
   width: 100%;
   height: auto;
   border: var(--theia-border-width) solid var(--theia-dropdown-border);
   border-radius: 4px;
+  position: relative;
   display: flex;
   flex-direction: column-reverse;
   overflow: hidden;
@@ -194,8 +216,8 @@ div:last-child > .theia-ChatNode {
 
 .theia-ChatInput-Editor-Placeholder {
   position: absolute;
-  top: -3px;
-  left: 19px;
+  top: 0;
+  left: 8px;
   right: 0;
   bottom: 0;
   display: flex;
@@ -205,6 +227,7 @@ div:last-child > .theia-ChatNode {
   z-index: 10;
   text-align: left;
 }
+
 .theia-ChatInput-Editor-Placeholder.hidden {
   display: none;
 }
@@ -269,6 +292,7 @@ div:last-child > .theia-ChatNode {
   border-radius: 5px;
   cursor: pointer;
 }
+
 .theia-CodePartRenderer-right .button:hover {
   background-color: var(--theia-toolbar-hoverBackground);
 }
@@ -355,9 +379,11 @@ details[open].collapsible-arguments .collapsible-arguments-summary {
 .theia-ResponseNode-ProgressMessage .inProgress {
   color: var(--theia-progressBar-background);
 }
+
 .theia-ResponseNode-ProgressMessage .completed {
   color: var(--theia-successBackground);
 }
+
 .theia-ResponseNode-ProgressMessage .failed {
   color: var(--theia-errorForeground);
 }
diff --git a/packages/ai-chat/src/common/chat-service.ts b/packages/ai-chat/src/common/chat-service.ts
index 3aeb8dcd612a0..075149bddbafa 100644
--- a/packages/ai-chat/src/common/chat-service.ts
+++ b/packages/ai-chat/src/common/chat-service.ts
@@ -35,6 +35,7 @@ import { ChatAgent, ChatAgentLocation } from './chat-agents';
 import { ParsedChatRequestAgentPart, ParsedChatRequestVariablePart, ParsedChatRequest } from './parsed-chat-request';
 import { AIVariableService } from '@theia/ai-core';
 import { Event } from '@theia/core/shared/vscode-languageserver-protocol';
+import { OrchestratorChatAgentId } from './orchestrator-chat-agent';
 
 export interface ChatRequestInvocation {
     /**
@@ -56,6 +57,7 @@ export interface ChatSession {
     title?: string;
     model: ChatModel;
     isActive: boolean;
+    pinnedAgent?: ChatAgent;
 }
 
 export interface ActiveSessionChangedEvent {
@@ -78,7 +80,7 @@ export interface ChatService {
 
     getSession(id: string): ChatSession | undefined;
     getSessions(): ChatSession[];
-    createSession(location?: ChatAgentLocation, options?: SessionOptions): ChatSession;
+    createSession(location?: ChatAgentLocation, options?: SessionOptions, pinnedAgent?: ChatAgent): ChatSession;
     deleteSession(sessionId: string): void;
     setActiveSession(sessionId: string, options?: SessionOptions): void;
 
@@ -122,12 +124,13 @@ export class ChatServiceImpl implements ChatService {
         return this._sessions.find(session => session.id === id);
     }
 
-    createSession(location = ChatAgentLocation.Panel, options?: SessionOptions): ChatSession {
+    createSession(location = ChatAgentLocation.Panel, options?: SessionOptions, pinnedAgent?: ChatAgent): ChatSession {
         const model = new ChatModelImpl(location);
         const session: ChatSessionInternal = {
             id: model.id,
             model,
-            isActive: true
+            isActive: true,
+            pinnedAgent: pinnedAgent
         };
         this._sessions.push(session);
         this.setActiveSession(session.id, options);
@@ -160,8 +163,14 @@ export class ChatServiceImpl implements ChatService {
         session.title = request.text;
 
         const parsedRequest = this.chatRequestParser.parseChatRequest(request, session.model.location);
+        let agent = this.getAgent(parsedRequest);
+
+        if (!session.pinnedAgent && agent && agent.id !== OrchestratorChatAgentId) {
+            session.pinnedAgent = agent;
+        } else if (session.pinnedAgent && this.getMentionedAgent(parsedRequest) === undefined) {
+            agent = session.pinnedAgent;
+        }
 
-        const agent = this.getAgent(parsedRequest);
         if (agent === undefined) {
             const error = 'No ChatAgents available to handle request!';
             this.logger.error(error);