diff --git a/src/settings/main.cpp b/src/settings/main.cpp
index 64458d6e4b..d861c72daf 100644
--- a/src/settings/main.cpp
+++ b/src/settings/main.cpp
@@ -8,6 +8,8 @@
 #include <common/dpi_aware.h>
 #include <common/common.h>
 
+#include "trace.h"
+
 #pragma comment(lib, "shlwapi.lib")
 #pragma comment(lib, "shcore.lib")
 #pragma comment(lib, "windowsapp")
@@ -272,6 +274,7 @@ void initialize_webview(int nShowCmd)
             else if (status == AsyncStatus::Error)
             {
                 MessageBox(NULL, L"Failed to create the WebView control.\nPlease report the bug to https://github.com/microsoft/PowerToys/issues", L"PowerToys Settings Error", MB_OK);
+                Trace::SettingsInitError(Trace::SettingsInitErrorCause::WebViewInitAsyncError);
                 exit(1);
             }
             else if (status == AsyncStatus::Started)
@@ -286,6 +289,7 @@ void initialize_webview(int nShowCmd)
     }
     catch (hresult_error const& e)
     {
+        Trace::SettingsInitError(Trace::SettingsInitErrorCause::WebViewInitWinRTException);
         WCHAR message[1024] = L"";
         StringCchPrintf(message, ARRAYSIZE(message), L"failed: %ls", e.message().c_str());
         MessageBox(g_main_wnd, message, L"Error", MB_OK);
@@ -553,6 +557,7 @@ bool initialize_com_security_policy_for_webview()
 
 int WINAPI WinMain(_In_ HINSTANCE hInstance, _In_opt_ HINSTANCE hPrevInstance, _In_ LPSTR lpCmdLine, _In_ int nShowCmd)
 {
+    Trace::RegisterProvider();
     CoInitialize(nullptr);
 
     const bool should_try_drop_privileges = !initialize_com_security_policy_for_webview() && is_process_elevated();
@@ -562,6 +567,7 @@ int WINAPI WinMain(_In_ HINSTANCE hInstance, _In_opt_ HINSTANCE hPrevInstance, _
         if (!drop_elevated_privileges())
         {
             MessageBox(NULL, L"Failed to drop admin privileges.\nPlease report the bug to https://github.com/microsoft/PowerToys/issues", L"PowerToys Settings Error", MB_OK);
+            Trace::SettingsInitError(Trace::SettingsInitErrorCause::FailedToDropPrivileges);
             exit(1);
         }
     }
@@ -585,5 +591,6 @@ int WINAPI WinMain(_In_ HINSTANCE hInstance, _In_opt_ HINSTANCE hPrevInstance, _
         DispatchMessage(&msg);
     }
 
+    Trace::UnregisterProvider();
     return (int)msg.wParam;
 }
diff --git a/src/settings/pch.h b/src/settings/pch.h
index ddb5596363..517a829af8 100644
--- a/src/settings/pch.h
+++ b/src/settings/pch.h
@@ -15,3 +15,4 @@
 #pragma pop_macro("GetCurrentTime")
 #include <strsafe.h>
 #include <Shlwapi.h>
+#include <ProjectTelemetry.h>
diff --git a/src/settings/settings.vcxproj b/src/settings/settings.vcxproj
index 1c1eca8fe2..bbc4ebc3a6 100644
--- a/src/settings/settings.vcxproj
+++ b/src/settings/settings.vcxproj
@@ -59,7 +59,7 @@
       <PrecompiledHeader>Use</PrecompiledHeader>
       <PrecompiledHeaderFile>pch.h</PrecompiledHeaderFile>
       <RuntimeLibrary>MultiThreadedDebug</RuntimeLibrary>
-      <AdditionalIncludeDirectories>..;%(AdditionalIncludeDirectories)</AdditionalIncludeDirectories>
+      <AdditionalIncludeDirectories>..;..\common\Telemetry;%(AdditionalIncludeDirectories)</AdditionalIncludeDirectories>
       <AdditionalOptions>/Zm150 %(AdditionalOptions)</AdditionalOptions>
     </ClCompile>
     <CustomBuildStep>
@@ -88,7 +88,7 @@
       <PrecompiledHeader>Use</PrecompiledHeader>
       <PrecompiledHeaderFile>pch.h</PrecompiledHeaderFile>
       <RuntimeLibrary>MultiThreaded</RuntimeLibrary>
-      <AdditionalIncludeDirectories>..;%(AdditionalIncludeDirectories)</AdditionalIncludeDirectories>
+      <AdditionalIncludeDirectories>..;..\common\Telemetry;%(AdditionalIncludeDirectories)</AdditionalIncludeDirectories>
       <AdditionalOptions>/Zm150 %(AdditionalOptions)</AdditionalOptions>
     </ClCompile>
     <Link>
@@ -113,6 +113,7 @@
     <ClInclude Include="pch.h" />
     <ClInclude Include="resource.h" />
     <ClInclude Include="StreamUriResolverFromFile.h" />
+    <ClInclude Include="trace.h" />
   </ItemGroup>
   <ItemGroup>
     <ClCompile Include="main.cpp" />
@@ -121,6 +122,7 @@
       <PrecompiledHeader Condition="'$(Configuration)|$(Platform)'=='Release|x64'">Create</PrecompiledHeader>
     </ClCompile>
     <ClCompile Include="StreamURIResolverFromFile.cpp" />
+    <ClCompile Include="trace.cpp" />
   </ItemGroup>
   <ItemGroup>
     <ResourceCompile Include="settings.rc" />
diff --git a/src/settings/settings.vcxproj.filters b/src/settings/settings.vcxproj.filters
index 586b68ec57..40f02e0184 100644
--- a/src/settings/settings.vcxproj.filters
+++ b/src/settings/settings.vcxproj.filters
@@ -24,6 +24,9 @@
     <ClInclude Include="resource.h">
       <Filter>Header Files</Filter>
     </ClInclude>
+    <ClInclude Include="trace.h">
+      <Filter>Header Files</Filter>
+    </ClInclude>
   </ItemGroup>
   <ItemGroup>
     <ClCompile Include="pch.cpp">
@@ -35,6 +38,9 @@
     <ClCompile Include="main.cpp">
       <Filter>Source Files</Filter>
     </ClCompile>
+    <ClCompile Include="trace.cpp">
+      <Filter>Source Files</Filter>
+    </ClCompile>
   </ItemGroup>
   <ItemGroup>
     <ResourceCompile Include="settings.rc">
diff --git a/src/settings/trace.cpp b/src/settings/trace.cpp
new file mode 100644
index 0000000000..1a29620665
--- /dev/null
+++ b/src/settings/trace.cpp
@@ -0,0 +1,45 @@
+#include "pch.h"
+#include "trace.h"
+
+TRACELOGGING_DEFINE_PROVIDER(
+    g_hProvider,
+    "Microsoft.PowerToys",
+    // {38e8889b-9731-53f5-e901-e8a7c1753074}
+    (0x38e8889b, 0x9731, 0x53f5, 0xe9, 0x01, 0xe8, 0xa7, 0xc1, 0x75, 0x30, 0x74),
+    TraceLoggingOptionProjectTelemetry());
+
+const char* settingsInitErrorCauseAsString(Trace::SettingsInitErrorCause error_case)
+{
+    switch (error_case)
+    {
+    case Trace::SettingsInitErrorCause::WebViewInitAsyncError:
+        return "WebViewInitAsyncError";
+    case Trace::SettingsInitErrorCause::WebViewInitWinRTException:
+        return "WebViewInitWinRTException";
+    case Trace::SettingsInitErrorCause::FailedToDropPrivileges:
+        return "FailedToDropPrivileges";
+    default:
+        return "UnknownError";
+    };
+}
+
+void Trace::SettingsInitError(const Trace::SettingsInitErrorCause error_cause)
+{
+    TraceLoggingWrite(
+        g_hProvider,
+        "PowerToysSettings_SettingsInitError",
+        TraceLoggingString(settingsInitErrorCauseAsString(error_cause), "Cause"),
+        ProjectTelemetryPrivacyDataTag(ProjectTelemetryTag_ProductAndServicePerformance),
+        TraceLoggingBoolean(TRUE, "UTCReplace_AppSessionGuid"),
+        TraceLoggingKeyword(PROJECT_KEYWORD_MEASURE));
+}
+
+void Trace::RegisterProvider() noexcept
+{
+    TraceLoggingRegister(g_hProvider);
+}
+
+void Trace::UnregisterProvider() noexcept
+{
+    TraceLoggingUnregister(g_hProvider);
+}
diff --git a/src/settings/trace.h b/src/settings/trace.h
new file mode 100644
index 0000000000..366b3fbda8
--- /dev/null
+++ b/src/settings/trace.h
@@ -0,0 +1,17 @@
+#pragma once
+
+class Trace
+{
+public:
+    enum class SettingsInitErrorCause : int32_t
+    {
+        WebViewInitAsyncError,
+        WebViewInitWinRTException,
+        FailedToDropPrivileges,
+    };
+
+    static void SettingsInitError(const SettingsInitErrorCause error_cause);
+
+    static void RegisterProvider() noexcept;
+    static void UnregisterProvider() noexcept;
+};