diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index c72e32c07e..85966d1045 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -10,6 +10,7 @@ env:
   Artifacts: ${{ github.workspace }}/artifacts/
   Coverage: ${{ github.workspace }}/coverage/
   DOTNET_SKIP_FIRST_TIME_EXPERIENCE: "true"
+  CLR_OPENSSL_VERSION_OVERRIDE: "1.1"
 defaults:
   run:
     shell: pwsh
@@ -27,7 +28,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        os: [ubuntu-20.04, windows-2022, macos-11]
+        os: [ubuntu-22.04, windows-2022, macos-13]
     name: 'Build'
     steps:
       - name: Checkout
diff --git a/.github/workflows/tests-net6.yml b/.github/workflows/tests-net6.yml
index 2672d41098..85e5141302 100644
--- a/.github/workflows/tests-net6.yml
+++ b/.github/workflows/tests-net6.yml
@@ -10,6 +10,7 @@ env:
   Artifacts: ${{ github.workspace }}/artifacts/
   Coverage: ${{ github.workspace }}/coverage/
   DOTNET_SKIP_FIRST_TIME_EXPERIENCE: "true"
+  CLR_OPENSSL_VERSION_OVERRIDE: "1.1"
 defaults:
   run:
     shell: pwsh
@@ -27,7 +28,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        os: [ubuntu-20.04, windows-2022, macos-11]
+        os: [ubuntu-22.04, windows-2022, macos-13]
         testProjects:
           - OmniSharp.MSBuild.Tests,OmniSharp.Roslyn.CSharp.Tests,OmniSharp.Cake.Tests,OmniSharp.Script.Tests,OmniSharp.Stdio.Tests,OmniSharp.Http.Tests,OmniSharp.Tests,OmniSharp.Lsp.Tests
           - OmniSharp.DotNetTest.Tests
diff --git a/.github/workflows/tests.yml b/.github/workflows/tests.yml
index b7f5d7ea1f..8ca5280290 100644
--- a/.github/workflows/tests.yml
+++ b/.github/workflows/tests.yml
@@ -27,7 +27,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        os: [ubuntu-20.04, windows-2022, macos-11]
+        os: [ubuntu-22.04, windows-2022, macos-13]
         testProjects:
           - OmniSharp.MSBuild.Tests,OmniSharp.Roslyn.CSharp.Tests,OmniSharp.Cake.Tests,OmniSharp.Script.Tests,OmniSharp.Stdio.Tests,OmniSharp.Http.Tests,OmniSharp.Tests,OmniSharp.Lsp.Tests
           - OmniSharp.DotNetTest.Tests
diff --git a/Directory.Packages.props b/Directory.Packages.props
index ee9fe8fafb..fbc957910e 100644
--- a/Directory.Packages.props
+++ b/Directory.Packages.props
@@ -9,7 +9,7 @@
         <MicrosoftTestPackageVersion>17.8.0</MicrosoftTestPackageVersion>
         <MSBuildPackageVersion>17.3.2</MSBuildPackageVersion>
         <NuGetPackageVersion>6.10.0-preview.1.18</NuGetPackageVersion>
-        <RoslynPackageVersion>4.10.0-2.24112.8</RoslynPackageVersion>
+        <RoslynPackageVersion>4.11.0-2.24266.3</RoslynPackageVersion>
         <XunitPackageVersion>2.6.1</XunitPackageVersion>
     </PropertyGroup>
 
diff --git a/azure-pipelines.yml b/azure-pipelines.yml
index a10f46cdf5..f27eb00668 100644
--- a/azure-pipelines.yml
+++ b/azure-pipelines.yml
@@ -55,7 +55,7 @@ jobs:
 
   - job: macOS
     pool:
-      vmImage: "macOS-11"
+      vmImage: "macos-13"
     dependsOn: GitVersion
     steps:
       - template: ./.pipelines/init.yml
@@ -76,7 +76,9 @@ jobs:
 
   - job: Linux
     pool:
-      vmImage: "ubuntu-20.04"
+      vmImage: "ubuntu-22.04"
+    variables:
+      CLR_OPENSSL_VERSION_OVERRIDE: '1.1'
     dependsOn: GitVersion
     steps:
       - template: ./.pipelines/init.yml
diff --git a/src/OmniSharp.Abstractions/Configuration.cs b/src/OmniSharp.Abstractions/Configuration.cs
index 51031d62b4..623fdb63ce 100644
--- a/src/OmniSharp.Abstractions/Configuration.cs
+++ b/src/OmniSharp.Abstractions/Configuration.cs
@@ -4,7 +4,7 @@ internal static class Configuration
     {
         public static bool ZeroBasedIndices = false;
 
-        public const string RoslynVersion = "4.10.0.0";
+        public const string RoslynVersion = "4.11.0.0";
         public const string RoslynPublicKeyToken = "31bf3856ad364e35";
 
         public readonly static string RoslynFeatures = GetRoslynAssemblyFullName("Microsoft.CodeAnalysis.Features");
diff --git a/tests/OmniSharp.Cake.Tests/BlockStructureFacts.cs b/tests/OmniSharp.Cake.Tests/BlockStructureFacts.cs
index a170950055..9dfd9d1ab3 100644
--- a/tests/OmniSharp.Cake.Tests/BlockStructureFacts.cs
+++ b/tests/OmniSharp.Cake.Tests/BlockStructureFacts.cs
@@ -38,7 +38,9 @@ void M()[|
                 .ToArray();
 
             var expected = testFile.Content.GetSpans()
-                .Select(span => testFile.Content.GetRangeFromSpan(span).ToRange()).ToArray();
+                .Select(span => testFile.Content.GetRangeFromSpan(span).ToRange())
+                .Reverse()
+                .ToArray();
 
             Assert.Equal(expected, lineSpans);
         }
diff --git a/tests/OmniSharp.MSBuild.Tests/AbstractMSBuildTestFixture.cs b/tests/OmniSharp.MSBuild.Tests/AbstractMSBuildTestFixture.cs
index 37c1cdc6d2..fcccd4d201 100644
--- a/tests/OmniSharp.MSBuild.Tests/AbstractMSBuildTestFixture.cs
+++ b/tests/OmniSharp.MSBuild.Tests/AbstractMSBuildTestFixture.cs
@@ -28,6 +28,7 @@ public AbstractMSBuildTestFixture(ITestOutputHelper output)
             // prerelease version so that our .NET 7 tests will pass.
             var configuration = new Dictionary<string, string>
             {
+                ["sdk:Version"] = "8.0.201",
                 ["sdk:IncludePrereleases"] = bool.TrueString
             }.ToConfiguration();
 
diff --git a/tests/OmniSharp.Roslyn.CSharp.Tests/BlockStructureFacts.cs b/tests/OmniSharp.Roslyn.CSharp.Tests/BlockStructureFacts.cs
index 2579e0baba..e4e165adeb 100644
--- a/tests/OmniSharp.Roslyn.CSharp.Tests/BlockStructureFacts.cs
+++ b/tests/OmniSharp.Roslyn.CSharp.Tests/BlockStructureFacts.cs
@@ -37,7 +37,9 @@ void M()[|
                 .ToArray();
 
             var expected = testFile.Content.GetSpans()
-                .Select(span => testFile.Content.GetRangeFromSpan(span).ToRange()).ToArray();
+                .Select(span => testFile.Content.GetRangeFromSpan(span).ToRange())
+                .Reverse()
+                .ToArray();
 
             Assert.Equal(expected, lineSpans);
         }