diff --git a/src/vs/workbench/contrib/chat/browser/actions/chatExecuteActions.ts b/src/vs/workbench/contrib/chat/browser/actions/chatExecuteActions.ts
index 69bccb4843b..56c8f5f25e0 100644
--- a/src/vs/workbench/contrib/chat/browser/actions/chatExecuteActions.ts
+++ b/src/vs/workbench/contrib/chat/browser/actions/chatExecuteActions.ts
@@ -513,7 +513,7 @@ export class CreateRemoteAgentJobAction extends Action2 {
 
 			const chatModel = widget.viewModel?.model;
 			const chatRequests = chatModel.getRequests();
-			const agents = remoteCodingAgent.getRegisteredAgents();
+			const agents = remoteCodingAgent.getAvailableAgents();
 			const defaultAgent = chatAgentService.getDefaultAgent(ChatAgentLocation.Panel);
 
 			const agent = agents[0]; // TODO: We just pick the first one for testing
diff --git a/src/vs/workbench/contrib/remoteCodingAgents/browser/remoteCodingAgents.contribution.ts b/src/vs/workbench/contrib/remoteCodingAgents/browser/remoteCodingAgents.contribution.ts
index 815d98a4a24..02b5833ccb1 100644
--- a/src/vs/workbench/contrib/remoteCodingAgents/browser/remoteCodingAgents.contribution.ts
+++ b/src/vs/workbench/contrib/remoteCodingAgents/browser/remoteCodingAgents.contribution.ts
@@ -76,13 +76,12 @@ export class RemoteCodingAgentsContribution extends Disposable implements IWorkb
 						continue;
 					}
 
-					// TODO: Handle 'when' clause
-
 					const agent: IRemoteCodingAgent = {
 						id: contribution.id,
 						command: contribution.command,
 						displayName: contribution.displayName,
-						description: contribution.description
+						description: contribution.description,
+						when: contribution.when
 					};
 					this.logService.info(`Registering remote coding agent: ${agent.displayName} (${agent.command})`);
 					this.remoteCodingAgentsService.registerAgent(agent);
diff --git a/src/vs/workbench/contrib/remoteCodingAgents/common/remoteCodingAgentsService.ts b/src/vs/workbench/contrib/remoteCodingAgents/common/remoteCodingAgentsService.ts
index 492d00d92b6..8ce3fd7361e 100644
--- a/src/vs/workbench/contrib/remoteCodingAgents/common/remoteCodingAgentsService.ts
+++ b/src/vs/workbench/contrib/remoteCodingAgents/common/remoteCodingAgentsService.ts
@@ -3,7 +3,9 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { IContextKey, IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
+import { Disposable } from '../../../../base/common/lifecycle.js';
+import { Event } from '../../../../base/common/event.js';
+import { ContextKeyExpr, IContextKey, IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
 import { InstantiationType, registerSingleton } from '../../../../platform/instantiation/common/extensions.js';
 import { createDecorator } from '../../../../platform/instantiation/common/instantiation.js';
 import { ChatContextKeys } from '../../chat/common/chatContextKeys.js';
@@ -13,37 +15,80 @@ export interface IRemoteCodingAgent {
 	command: string;
 	displayName: string;
 	description?: string;
+	when?: string;
 }
 
 export interface IRemoteCodingAgentsService {
 	readonly _serviceBrand: undefined;
 	getRegisteredAgents(): IRemoteCodingAgent[];
+	getAvailableAgents(): IRemoteCodingAgent[];
 	registerAgent(agent: IRemoteCodingAgent): void;
 }
 
 export const IRemoteCodingAgentsService = createDecorator<IRemoteCodingAgentsService>('remoteCodingAgentsService');
 
-export class RemoteCodingAgentsService implements IRemoteCodingAgentsService {
+export class RemoteCodingAgentsService extends Disposable implements IRemoteCodingAgentsService {
 	readonly _serviceBrand: undefined;
 	private readonly _ctxHasRemoteCodingAgent: IContextKey<boolean>;
+	private readonly agents: IRemoteCodingAgent[] = [];
+	private readonly contextKeys = new Set<string>();
 
 	constructor(
 		@IContextKeyService private readonly contextKeyService: IContextKeyService
 	) {
+		super();
 		this._ctxHasRemoteCodingAgent = ChatContextKeys.hasRemoteCodingAgent.bindTo(this.contextKeyService);
+
+		// Listen for context changes and re-evaluate agent availability
+		this._register(Event.filter(contextKeyService.onDidChangeContext, e => e.affectsSome(this.contextKeys))(() => {
+			this.updateContextKeys();
+		}));
 	}
 
-	private agents: IRemoteCodingAgent[] = [];
-
 	getRegisteredAgents(): IRemoteCodingAgent[] {
-		return this.agents;
+		return [...this.agents];
+	}
+
+	getAvailableAgents(): IRemoteCodingAgent[] {
+		return this.agents.filter(agent => this.isAgentAvailable(agent));
 	}
 
 	registerAgent(agent: IRemoteCodingAgent): void {
-		if (!this.agents.includes(agent)) {
+		// Check if agent already exists
+		const existingIndex = this.agents.findIndex(a => a.id === agent.id);
+		if (existingIndex >= 0) {
+			// Update existing agent
+			this.agents[existingIndex] = agent;
+		} else {
+			// Add new agent
 			this.agents.push(agent);
-			this._ctxHasRemoteCodingAgent.set(true);
 		}
+
+		// Track context keys from the when condition
+		if (agent.when) {
+			const whenExpr = ContextKeyExpr.deserialize(agent.when);
+			if (whenExpr) {
+				for (const key of whenExpr.keys()) {
+					this.contextKeys.add(key);
+				}
+			}
+		}
+
+		this.updateContextKeys();
+	}
+
+	private isAgentAvailable(agent: IRemoteCodingAgent): boolean {
+		if (!agent.when) {
+			return true;
+		}
+
+		const whenExpr = ContextKeyExpr.deserialize(agent.when);
+		return !whenExpr || this.contextKeyService.contextMatchesRules(whenExpr);
+	}
+
+	private updateContextKeys(): void {
+		const hasAvailableAgent = this.getAvailableAgents().length > 0;
+		this._ctxHasRemoteCodingAgent.set(hasAvailableAgent);
 	}
 }