diff --git a/ui/desktop/index.html b/ui/desktop/index.html
index 3f8c17512877..f606653e47eb 100644
--- a/ui/desktop/index.html
+++ b/ui/desktop/index.html
@@ -2,7 +2,7 @@
 <html>
   <head>
     <meta charset="UTF-8" />
-    <meta http-equiv="Content-Security-Policy" content="default-src 'self'; style-src 'self' 'unsafe-inline'; script-src 'self' 'unsafe-inline'; img-src 'self' data: https:; connect-src 'self' http://127.0.0.1:* https://api.github.com https://github.com https://objects.githubusercontent.com; object-src 'none'; frame-src 'none'; font-src 'self' data: https:; media-src 'self' mediastream:; form-action 'none'; base-uri 'self'; manifest-src 'self'; worker-src 'self';" />
+    <meta http-equiv="Content-Security-Policy" content="default-src 'self'; style-src 'self' 'unsafe-inline'; script-src 'self' 'unsafe-inline'; img-src 'self' data: https:; connect-src 'self' http://127.0.0.1:* https:; object-src 'none'; frame-src 'none'; font-src 'self' data: https:; media-src 'self' mediastream:; form-action 'none'; base-uri 'self'; manifest-src 'self'; worker-src 'self';" />
     <title>Goose</title>
     <script>
       // Initialize theme before any content loads
diff --git a/ui/desktop/src/components/settings/sessions/SessionSharingSection.tsx b/ui/desktop/src/components/settings/sessions/SessionSharingSection.tsx
index 2c0556042b9f..ba42d264e201 100644
--- a/ui/desktop/src/components/settings/sessions/SessionSharingSection.tsx
+++ b/ui/desktop/src/components/settings/sessions/SessionSharingSection.tsx
@@ -1,6 +1,6 @@
 import React, { useState, useEffect } from 'react';
 import { Input } from '../../ui/input';
-import { Check, Lock } from 'lucide-react';
+import { Check, Lock, Loader2, AlertCircle } from 'lucide-react';
 import { Switch } from '../../ui/switch';
 import { Button } from '../../ui/button';
 import { Card, CardContent, CardDescription, CardHeader, CardTitle } from '../../ui/card';
@@ -15,6 +15,11 @@ export default function SessionSharingSection() {
     baseUrl: typeof envBaseUrlShare === 'string' ? envBaseUrlShare : '',
   });
   const [urlError, setUrlError] = useState('');
+  const [testResult, setTestResult] = useState<{
+    status: 'success' | 'error' | 'testing' | null;
+    message: string;
+  }>({ status: null, message: '' });
+
   // isUrlConfigured is true if the user has configured a baseUrl and it is valid.
   const isUrlConfigured =
     !envBaseUrlShare &&
@@ -74,6 +79,9 @@ export default function SessionSharingSection() {
       baseUrl: newBaseUrl,
     }));
 
+    // Clear previous test results when URL changes
+    setTestResult({ status: null, message: '' });
+
     if (isValidUrl(newBaseUrl)) {
       setUrlError('');
       const updated = { ...sessionSharingConfig, baseUrl: newBaseUrl };
@@ -83,13 +91,72 @@ export default function SessionSharingSection() {
     }
   };
 
+  // Test connection to the configured URL
+  const testConnection = async () => {
+    const baseUrl = sessionSharingConfig.baseUrl;
+    if (!baseUrl) return;
+
+    setTestResult({ status: 'testing', message: 'Testing connection...' });
+
+    try {
+      // Create an AbortController for timeout
+      const controller = new AbortController();
+      const timeoutId = window.setTimeout(() => controller.abort(), 10000); // 10 second timeout
+
+      const response = await fetch(baseUrl, {
+        method: 'GET',
+        headers: {
+          Accept: 'application/json, text/plain, */*',
+        },
+        signal: controller.signal,
+      });
+
+      window.clearTimeout(timeoutId);
+
+      // Consider any response (even 404) as a successful connection
+      // since it means we can reach the server
+      if (response.status < 500) {
+        setTestResult({
+          status: 'success',
+          message: `Connection successful! Server responded with status ${response.status}.`,
+        });
+      } else {
+        setTestResult({
+          status: 'error',
+          message: `Server error: HTTP ${response.status}. The server may not be configured correctly.`,
+        });
+      }
+    } catch (error) {
+      console.error('Connection test failed:', error);
+      let errorMessage = 'Connection failed. ';
+
+      if (error instanceof TypeError && error.message.includes('fetch')) {
+        errorMessage +=
+          'Unable to reach the server. Please check the URL and your network connection.';
+      } else if (error instanceof Error) {
+        if (error.name === 'AbortError') {
+          errorMessage += 'Connection timed out. The server may be slow or unreachable.';
+        } else {
+          errorMessage += error.message;
+        }
+      } else {
+        errorMessage += 'Unknown error occurred.';
+      }
+
+      setTestResult({
+        status: 'error',
+        message: errorMessage,
+      });
+    }
+  };
+
   return (
     <section id="session-sharing" className="space-y-4 pr-4 mt-1">
       <Card className="pb-2">
         <CardHeader className="pb-0">
           <CardTitle>Session Sharing</CardTitle>
           <CardDescription>
-            {envBaseUrlShare
+            {(envBaseUrlShare as string)
               ? 'Session sharing is configured but fully opt-in — your sessions are only shared when you explicitly click the share button.'
               : 'You can enable session sharing to share your sessions with others.'}
           </CardDescription>
@@ -99,7 +166,7 @@ export default function SessionSharingSection() {
             {/* Toggle for enabling session sharing */}
             <div className="flex items-center gap-3">
               <label className="text-sm cursor-pointer">
-                {envBaseUrlShare
+                {(envBaseUrlShare as string)
                   ? 'Session sharing has already been configured'
                   : 'Enable session sharing'}
               </label>
@@ -136,19 +203,44 @@ export default function SessionSharingSection() {
                   />
                 </div>
                 {urlError && <p className="text-red-500 text-sm">{urlError}</p>}
-                {isUrlConfigured && (
-                  <Button
-                    variant="outline"
-                    size="sm"
-                    className="mt-2"
-                    onClick={() => {
-                      // Test the connection to the configured URL
-                      console.log('Testing connection to:', sessionSharingConfig.baseUrl);
-                      // TODO: Implement actual connection test
-                    }}
-                  >
-                    Test Connection
-                  </Button>
+
+                {(isUrlConfigured || (envBaseUrlShare as string)) && (
+                  <div className="space-y-2">
+                    <Button
+                      variant="outline"
+                      size="sm"
+                      onClick={testConnection}
+                      disabled={testResult.status === 'testing'}
+                      className="flex items-center gap-2"
+                    >
+                      {testResult.status === 'testing' ? (
+                        <>
+                          <Loader2 className="w-4 h-4 animate-spin" />
+                          Testing...
+                        </>
+                      ) : (
+                        'Test Connection'
+                      )}
+                    </Button>
+
+                    {/* Test Results */}
+                    {testResult.status && testResult.status !== 'testing' && (
+                      <div
+                        className={`flex items-start gap-2 p-3 rounded-md text-sm ${
+                          testResult.status === 'success'
+                            ? 'bg-green-50 text-green-800 border border-green-200'
+                            : 'bg-red-50 text-red-800 border border-red-200'
+                        }`}
+                      >
+                        {testResult.status === 'success' ? (
+                          <Check className="w-4 h-4 mt-0.5 flex-shrink-0" />
+                        ) : (
+                          <AlertCircle className="w-4 h-4 mt-0.5 flex-shrink-0" />
+                        )}
+                        <span>{testResult.message}</span>
+                      </div>
+                    )}
+                  </div>
                 )}
               </div>
             )}
diff --git a/ui/desktop/src/main.ts b/ui/desktop/src/main.ts
index f3745ac4b073..18f1769e2ac7 100644
--- a/ui/desktop/src/main.ts
+++ b/ui/desktop/src/main.ts
@@ -874,9 +874,43 @@ const openDirectoryDialog = async (
 
     addRecentDir(dirToAdd);
     const currentWindow = BrowserWindow.getFocusedWindow();
-    await createChat(app, undefined, dirToAdd);
+
     if (replaceWindow && currentWindow) {
+      // Replace current window with new one
+      await createChat(app, undefined, dirToAdd);
       currentWindow.close();
+    } else {
+      // Update the working directory in the current window's localStorage
+      if (currentWindow) {
+        try {
+          const updateConfigScript = `
+            try {
+              const currentConfig = JSON.parse(localStorage.getItem('gooseConfig') || '{}');
+              const updatedConfig = {
+                ...currentConfig,
+                GOOSE_WORKING_DIR: '${dirToAdd.replace(/'/g, "\\'")}',
+              };
+              localStorage.setItem('gooseConfig', JSON.stringify(updatedConfig));
+              
+              // Trigger a config update event so the UI can refresh
+              window.dispatchEvent(new CustomEvent('goose-config-updated', { 
+                detail: { GOOSE_WORKING_DIR: '${dirToAdd.replace(/'/g, "\\'")}' } 
+              }));
+            } catch (e) {
+              console.error('Failed to update working directory in localStorage:', e);
+            }
+          `;
+          await currentWindow.webContents.executeJavaScript(updateConfigScript);
+          console.log(`Updated working directory to: ${dirToAdd}`);
+        } catch (error) {
+          console.error('Failed to update working directory:', error);
+          // Fallback: create new window
+          await createChat(app, undefined, dirToAdd);
+        }
+      } else {
+        // No current window, create new one
+        await createChat(app, undefined, dirToAdd);
+      }
     }
   }
   return result;
