diff --git a/src/extension.ts b/src/extension.ts
index 1136f02..d65467c 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -8,7 +8,7 @@ import { Logging, setDebug } from './logging';
 import { Manager } from './manager';
 import type { SSHPseudoTerminal } from './pseudoTerminal';
 import { ConfigTreeProvider, ConnectionTreeProvider } from './treeViewManager';
-import { pickComplex, PickComplexOptions, pickConnection, setAsAbsolutePath } from './ui-utils';
+import { pickComplex, PickComplexOptions, pickConnection, setAsAbsolutePath, setupWhenClauseContexts } from './ui-utils';
 
 function getVersion(): string | undefined {
   const ext = vscode.extensions.getExtension('Kelvin.vscode-sshfs');
@@ -59,6 +59,8 @@ export function activate(context: vscode.ExtensionContext) {
   subscribe(vscode.tasks.registerTaskProvider('ssh-shell', manager));
   subscribe(vscode.window.registerTerminalLinkProvider(manager));
 
+  setupWhenClauseContexts(manager.connectionManager);
+
   function registerCommandHandler(name: string, handler: CommandHandler) {
     const callback = async (arg?: string | FileSystemConfig | Connection | SSHPseudoTerminal | vscode.Uri) => {
       if (handler.promptOptions && (!arg || typeof arg === 'string')) {
diff --git a/src/ui-utils.ts b/src/ui-utils.ts
index 1eccf9d..d3e9828 100644
--- a/src/ui-utils.ts
+++ b/src/ui-utils.ts
@@ -1,7 +1,7 @@
 
 import * as vscode from 'vscode';
 import { getConfigs } from './config';
-import type { Connection } from './connection';
+import type { Connection, ConnectionManager } from './connection';
 import { parseConnectionString, FileSystemConfig } from './fileSystemConfig';
 import type { Manager } from './manager';
 import type { SSHPseudoTerminal } from './pseudoTerminal';
@@ -18,6 +18,25 @@ export function formatAddress(config: FileSystemConfig): string {
     return `${username ? `${username}@` : ''}${host}${port ? `:${port}` : ''}`;
 }
 
+export function setWhenClauseContext(key: string, value: any) {
+    return vscode.commands.executeCommand('setContext', `sshfs.${key}`, value);
+}
+
+export function setupWhenClauseContexts(connectionManager: ConnectionManager): Promise<void> {
+    async function refresh() {
+        const active = connectionManager.getActiveConnections();
+        const pending = connectionManager.getPendingConnections();
+        await setWhenClauseContext('openConnections', active.length + pending.length);
+        await setWhenClauseContext('openTerminals', active.reduce((tot, con) => tot + con.terminals.length, 0));
+        await setWhenClauseContext('openFileSystems', active.reduce((tot, con) => tot + con.filesystems.length, 0));
+    }
+    connectionManager.onConnectionAdded(refresh);
+    connectionManager.onConnectionRemoved(refresh);
+    connectionManager.onConnectionUpdated(refresh);
+    connectionManager.onPendingChanged(refresh);
+    return refresh();
+}
+
 export let asAbsolutePath: vscode.ExtensionContext['asAbsolutePath'] | undefined;
 export const setAsAbsolutePath = (value: typeof asAbsolutePath) => asAbsolutePath = value;