diff --git a/src/Cody.VisualStudio.Tests/ChatLoggedBasicTests.cs b/src/Cody.VisualStudio.Tests/ChatLoggedBasicTests.cs
index 5a9dc1fd..f9775d07 100644
--- a/src/Cody.VisualStudio.Tests/ChatLoggedBasicTests.cs
+++ b/src/Cody.VisualStudio.Tests/ChatLoggedBasicTests.cs
@@ -31,6 +31,8 @@ public async Task Active_File_Name_And_Line_Selection_Is_Showing_In_Chat_Input()
         {
             // given
             await WaitForPlaywrightAsync();
+            await NewChat();
+
             await OpenSolution(SolutionsPaths.GetConsoleApp1File("ConsoleApp1.sln"));
 
             // when
@@ -46,6 +48,28 @@ public async Task Active_File_Name_And_Line_Selection_Is_Showing_In_Chat_Input()
             Assert.Equal(endLine, secondTag.EndLine);
         }
 
+        [VsFact(Version = VsVersion.VS2022)]
+        public async Task Active_File_Match_Current_Chat_Context()
+        {
+            // given
+            await WaitForPlaywrightAsync();
+            await NewChat();
+
+            await OpenSolution(SolutionsPaths.GetConsoleApp1File("ConsoleApp1.sln"));
+
+            // when
+            const int startLine = 2; const int endLine = 3;
+            await OpenDocument(SolutionsPaths.GetConsoleApp1File(@"ConsoleApp1\Program.cs"), startLine, endLine);
+            var tags = await GetChatContextTags();
+
+            // then
+            var firstTagName = tags.First().Name;
+            var secondTag = tags.ElementAt(1);
+            Assert.Equal("Program.cs", firstTagName);
+            Assert.Equal(startLine, secondTag.StartLine);
+            Assert.Equal(endLine, secondTag.EndLine);
+        }
+
         [VsFact(Version = VsVersion.VS2022)]
         public async Task Can_Chat_Tool_Window_Be_Closed_And_Opened_Again()
         {
@@ -60,7 +84,7 @@ public async Task Can_Chat_Tool_Window_Be_Closed_And_Opened_Again()
             Assert.True(isOpen);
         }
 
-        //[VsFact(Version = VsVersion.VS2022)]
+        [VsFact(Version = VsVersion.VS2022)]
         public async Task Entered_Prompt_Show_Up_In_Today_History()
         {
             var num = new Random().Next();
@@ -69,14 +93,11 @@ public async Task Entered_Prompt_Show_Up_In_Today_History()
             await WaitForPlaywrightAsync();
 
             await EnterChatTextAndSend(prompt);
-            await CloseCodyChatToolWindow();
 
-            await OpenCodyChatToolWindow();
             await ShowHistoryTab();
             var chatHistoryEntries = await GetTodayChatHistory();
 
             Assert.Contains(chatHistoryEntries, x => x.Contains(prompt));
-
         }
 
         public void Dispose()
diff --git a/src/Cody.VisualStudio.Tests/PlaywrightTestsBase.cs b/src/Cody.VisualStudio.Tests/PlaywrightTestsBase.cs
index ee82108a..2652e5d2 100644
--- a/src/Cody.VisualStudio.Tests/PlaywrightTestsBase.cs
+++ b/src/Cody.VisualStudio.Tests/PlaywrightTestsBase.cs
@@ -142,7 +142,18 @@ protected async Task AssertTextIsPresent(string text)
             Assert.Equal(text, textContents.First());
         }
 
-        protected async Task ShowChatTab() => await Page.GetByTestId("tab-chat").ClickAsync();
+        protected async Task ShowChatTab()
+        {
+            await Page.GetByTestId("tab-chat").ClickAsync();
+            await Task.Delay(500);
+        }
+
+        protected async Task NewChat()
+        {
+            await Page.GetByRole(AriaRole.Button, new PageGetByRoleOptions {Name = "New Chat"}).ClickAsync();
+
+            await Task.Delay(500);
+        }
 
         protected async Task ShowHistoryTab()
         {
@@ -158,15 +169,21 @@ protected async Task ShowHistoryTab()
 
         protected async Task EnterChatTextAndSend(string prompt)
         {
-            var entryArea = Page.Locator("[data-keep-toolbar-open=true]").Last;
-
-            await entryArea.PressSequentiallyAsync(prompt);
-            await entryArea.PressAsync("Enter");
+            var entryArea = Page.Locator("span[data-lexical-text='true']");
+            var enterArea = Page.Locator("[data-keep-toolbar-open=true]").Last;
 
-            var button = await Page.WaitForSelectorAsync("menu button[type=submit][title=Stop]");
+            await entryArea.FillAsync(prompt);
+            await enterArea.PressAsync("Enter");
 
-            while (await button.GetAttributeAsync("title") == "Stop") await Task.Delay(500);
+            var isStopVisible = false; 
+            while (!isStopVisible)
+            {
+                isStopVisible = await Page.Locator("vscode-button").First.IsVisibleAsync();
+                await Task.Delay(500);
+            }
             await Task.Delay(500);
+
+            await DismissStartWindow();
         }
 
         protected async Task<string[]> GetTodayChatHistory()
@@ -182,6 +199,7 @@ protected async Task<string[]> GetTodayChatHistory()
         protected async Task<IReadOnlyCollection<ContextTag>> GetChatContextTags()
         {
             var tagsList = new List<ContextTag>();
+            await ShowChatTab();
 
             WriteLog("Searching for Chat ...");
             var chatBox = await Page.QuerySelectorAsync("[aria-label='Chat message']");
diff --git a/src/Cody.VisualStudio/Services/ThemeService.cs b/src/Cody.VisualStudio/Services/ThemeService.cs
index 2312e47e..1a7a9bef 100644
--- a/src/Cody.VisualStudio/Services/ThemeService.cs
+++ b/src/Cody.VisualStudio/Services/ThemeService.cs
@@ -130,10 +130,14 @@ public string GetThemingScript()
 
             // Generate the CSS variables for the fonts.
             var editorFont = GetEditorFont();
+            _logger.Debug($"Detected editor font:{editorFont.FontName} size:{editorFont.Size}");
+
             sb.AppendLine($"rootStyle.setProperty('--visualstudio-editor-font-family', '{editorFont.FontName}');");
             sb.AppendLine($"rootStyle.setProperty('--visualstudio-editor-font-size', '{editorFont.Size}pt');");
 
             var uiFont = GetUIFont();
+            _logger.Debug($"Detected UI font:{uiFont.FontName} size:{uiFont.Size}");
+
             sb.AppendLine($"rootStyle.setProperty('--visualstudio-ui-font-family', '{uiFont.FontName}');");
             sb.AppendLine($"rootStyle.setProperty('--visualstudio-ui-font-size', '{uiFont.Size}pt');");