diff --git a/test/PowerShellEditorServices.Test.E2E/LanguageServerProtocolMessageTests.cs b/test/PowerShellEditorServices.Test.E2E/LanguageServerProtocolMessageTests.cs
index 02767023c..91704bd84 100644
--- a/test/PowerShellEditorServices.Test.E2E/LanguageServerProtocolMessageTests.cs
+++ b/test/PowerShellEditorServices.Test.E2E/LanguageServerProtocolMessageTests.cs
@@ -1030,12 +1030,19 @@ await PsesLanguageClient
                 });
         }
 
-        [SkippableFact]
+        [Fact]
         public async Task CanSendCompletionAndCompletionResolveRequestAsync()
         {
-            Skip.If(IsLinux, "This depends on the help system, which is flaky on Linux.");
-            Skip.If(PsesStdioLanguageServerProcessHost.IsWindowsPowerShell, "This help system isn't updated in CI.");
-            string filePath = NewTestFile("Write-H");
+            await PsesLanguageClient
+            .SendRequest(
+                "evaluate",
+                new EvaluateRequestArguments
+                {
+                    Expression = $"Update-Help Microsoft.Powershell.Utility -SourcePath {s_binDir};"
+                })
+            .ReturningVoid(CancellationToken.None);
+
+            string filePath = NewTestFile("Get-Date");
 
             CompletionList completionItems = await PsesLanguageClient.TextDocument.RequestCompletion(
                 new CompletionParams
@@ -1048,16 +1055,16 @@ public async Task CanSendCompletionAndCompletionResolveRequestAsync()
                 });
 
             CompletionItem completionItem = Assert.Single(completionItems,
-                completionItem1 => completionItem1.FilterText == "Write-Host");
+                completionItem1 => completionItem1.FilterText == "Get-Date");
 
             CompletionItem updatedCompletionItem = await PsesLanguageClient
                 .SendRequest("completionItem/resolve", completionItem)
                 .Returning<CompletionItem>(CancellationToken.None);
 
-            Assert.Contains("Writes customized output to a host", updatedCompletionItem.Documentation.String);
+            Assert.Contains("Gets the current date and time.", updatedCompletionItem.Documentation.String);
         }
 
-        [SkippableFact(Skip = "Completion for Expand-SlowArchive is flaky.")]
+        [Fact]
         public async Task CanSendCompletionResolveWithModulePrefixRequestAsync()
         {
             await PsesLanguageClient
@@ -1065,11 +1072,11 @@ await PsesLanguageClient
                     "evaluate",
                     new EvaluateRequestArguments
                     {
-                        Expression = "Import-Module Microsoft.PowerShell.Archive -Prefix Slow"
+                        Expression = $"Update-Help Microsoft.Powershell.Utility -SourcePath {s_binDir};Import-Module Microsoft.PowerShell.Utility -Prefix Test -Force"
                     })
                 .ReturningVoid(CancellationToken.None);
 
-            string filePath = NewTestFile("Expand-SlowArch");
+            string filePath = NewTestFile("Get-TestDate");
 
             CompletionList completionItems = await PsesLanguageClient.TextDocument.RequestCompletion(
                 new CompletionParams
@@ -1078,17 +1085,15 @@ await PsesLanguageClient
                     {
                         Uri = DocumentUri.FromFileSystemPath(filePath)
                     },
-                    Position = new Position(line: 0, character: 15)
+                    Position = new Position(line: 0, character: 12)
                 });
 
             CompletionItem completionItem = Assert.Single(completionItems,
-                completionItem1 => completionItem1.Label == "Expand-SlowArchive");
+                completionItem1 => completionItem1.Label == "Get-TestDate");
 
-            CompletionItem updatedCompletionItem = await PsesLanguageClient
-                .SendRequest("completionItem/resolve", completionItem)
-                .Returning<CompletionItem>(CancellationToken.None);
+            CompletionItem updatedCompletionItem = await PsesLanguageClient.ResolveCompletion(completionItem);
 
-            Assert.Contains("Extracts files from a specified archive", updatedCompletionItem.Documentation.String);
+            Assert.Contains("Gets the current date and time.", updatedCompletionItem.Documentation.String);
         }
 
         [SkippableFact]
@@ -1123,22 +1128,21 @@ public async Task CanSendSignatureHelpRequestAsync()
         {
             string filePath = NewTestFile("Get-Date -");
 
-            SignatureHelp signatureHelp = await PsesLanguageClient
-                .SendRequest(
-                    "textDocument/signatureHelp",
-                    new SignatureHelpParams
+            SignatureHelp signatureHelp = await PsesLanguageClient.RequestSignatureHelp
+            (
+                new SignatureHelpParams
+                {
+                    TextDocument = new TextDocumentIdentifier
                     {
-                        TextDocument = new TextDocumentIdentifier
-                        {
-                            Uri = new Uri(filePath)
-                        },
-                        Position = new Position
-                        {
-                            Line = 0,
-                            Character = 10
-                        }
-                    })
-                .Returning<SignatureHelp>(CancellationToken.None);
+                        Uri = new Uri(filePath)
+                    },
+                    Position = new Position
+                    {
+                        Line = 0,
+                        Character = 10
+                    }
+                }
+            );
 
             Assert.Contains("Get-Date", signatureHelp.Signatures.First().Label);
         }
@@ -1231,7 +1235,7 @@ await PsesLanguageClient
             Assert.Equal(0, evaluateResponseBody.VariablesReference);
         }
 
-        [Fact]
+        [Fact(Timeout = 60000)]
         public async Task CanSendGetCommandRequestAsync()
         {
             List<object> pSCommandMessages =
diff --git a/test/PowerShellEditorServices.Test.E2E/PowerShellEditorServices.Test.E2E.csproj b/test/PowerShellEditorServices.Test.E2E/PowerShellEditorServices.Test.E2E.csproj
index 2ea39d3fd..3f110f212 100644
--- a/test/PowerShellEditorServices.Test.E2E/PowerShellEditorServices.Test.E2E.csproj
+++ b/test/PowerShellEditorServices.Test.E2E/PowerShellEditorServices.Test.E2E.csproj
@@ -1,5 +1,6 @@
 <Project Sdk="Microsoft.NET.Sdk">
-  <Import Project="$([MSBuild]::GetDirectoryNameOfFileAbove($(MSBuildThisFileDirectory), PowerShellEditorServices.Common.props))\PowerShellEditorServices.Common.props" />
+  <Import
+    Project="$([MSBuild]::GetDirectoryNameOfFileAbove($(MSBuildThisFileDirectory), PowerShellEditorServices.Common.props))\PowerShellEditorServices.Common.props" />
 
   <PropertyGroup>
     <TargetFrameworks>net8.0</TargetFrameworks>
@@ -18,8 +19,10 @@
   <Choose>
     <When Condition=" '$(LocalOmniSharp)' == 'true' ">
       <ItemGroup>
-        <ProjectReference Include="..\..\..\csharp-language-server-protocol\src\Client\Client.csproj" />
-        <ProjectReference Include="..\..\..\csharp-language-server-protocol\src\Dap.Client\Dap.client.csproj" />
+        <ProjectReference
+          Include="..\..\..\csharp-language-server-protocol\src\Client\Client.csproj" />
+        <ProjectReference
+          Include="..\..\..\csharp-language-server-protocol\src\Dap.Client\Dap.client.csproj" />
       </ItemGroup>
     </When>
     <Otherwise>
@@ -37,4 +40,11 @@
   <ItemGroup>
     <Content Include="xunit.runner.json" CopyToOutputDirectory="PreserveNewest" />
   </ItemGroup>
+
+  <ItemGroup>
+    <!-- Used for Update-Help for some test fixtures -->
+    <Content Include="..\PowerShellEditorServices.Test.Shared\PSHelp\**\*"
+      CopyToOutputDirectory="PreserveNewest" />
+  </ItemGroup>
+
 </Project>
diff --git a/test/PowerShellEditorServices.Test.E2E/xunit.runner.json b/test/PowerShellEditorServices.Test.E2E/xunit.runner.json
index 09cc13a99..f1c3b37cd 100644
--- a/test/PowerShellEditorServices.Test.E2E/xunit.runner.json
+++ b/test/PowerShellEditorServices.Test.E2E/xunit.runner.json
@@ -2,8 +2,9 @@
   "$schema": "https://xunit.net/schema/current/xunit.runner.schema.json",
   "appDomain": "denied",
   "parallelizeTestCollections": true,
-  "parallelAlgorithm": "aggressive",
+  "parallelAlgorithm": "conservative",
   "methodDisplay": "method",
   "diagnosticMessages": true,
-  "longRunningTestSeconds": 60
+  "longRunningTestSeconds": 10,
+  "showLiveOutput": true
 }
diff --git a/test/PowerShellEditorServices.Test.Shared/PSHelp/Microsoft.PowerShell.Utility_1da87e53-152b-403e-98dc-74d7b4d63d59_HelpInfo.xml b/test/PowerShellEditorServices.Test.Shared/PSHelp/Microsoft.PowerShell.Utility_1da87e53-152b-403e-98dc-74d7b4d63d59_HelpInfo.xml
new file mode 100644
index 000000000..1b6473db8
--- /dev/null
+++ b/test/PowerShellEditorServices.Test.Shared/PSHelp/Microsoft.PowerShell.Utility_1da87e53-152b-403e-98dc-74d7b4d63d59_HelpInfo.xml
@@ -0,0 +1,10 @@
+<?xml version="1.0" encoding="utf-8"?>
+<HelpInfo xmlns="http://schemas.microsoft.com/powershell/help/2010/05">
+  <HelpContentURI>https://aka.ms/powershell51-help</HelpContentURI>
+  <SupportedUICultures>
+    <UICulture>
+      <UICultureName>en-US</UICultureName>
+      <UICultureVersion>5.2.0.0</UICultureVersion>
+    </UICulture>
+  </SupportedUICultures>
+</HelpInfo>
\ No newline at end of file
diff --git a/test/PowerShellEditorServices.Test.Shared/PSHelp/Microsoft.PowerShell.Utility_1da87e53-152b-403e-98dc-74d7b4d63d59_en-US_HelpContent.cab b/test/PowerShellEditorServices.Test.Shared/PSHelp/Microsoft.PowerShell.Utility_1da87e53-152b-403e-98dc-74d7b4d63d59_en-US_HelpContent.cab
new file mode 100644
index 000000000..7c4175b2e
Binary files /dev/null and b/test/PowerShellEditorServices.Test.Shared/PSHelp/Microsoft.PowerShell.Utility_1da87e53-152b-403e-98dc-74d7b4d63d59_en-US_HelpContent.cab differ
diff --git a/test/PowerShellEditorServices.Test.Shared/PSHelp/README b/test/PowerShellEditorServices.Test.Shared/PSHelp/README
new file mode 100644
index 000000000..57c3e6007
--- /dev/null
+++ b/test/PowerShellEditorServices.Test.Shared/PSHelp/README
@@ -0,0 +1 @@
+Windows PowerShell does not have updated help in CI by default and we utilize a private Azure Devops repo for builds that has no internet access. The completion tests validate the Windows Help so we update it offline from here so these tests can work.