diff --git a/CHANGELOG.md b/CHANGELOG.md
index bcd5653686..4b20965abe 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,10 @@
 
 ## Unreleased
 
+### Fixes
+
+- Partial workaround for MAX_PATH issues when building iOS applications from Windows ([#4533](https://github.com/getsentry/sentry-dotnet/pull/4533))
+
 ### Dependencies
 
 - Bump Java SDK from v8.22.0 to v8.23.0 ([#4586](https://github.com/getsentry/sentry-dotnet/pull/4586))
diff --git a/src/Sentry.Bindings.Cocoa/ApiDefinitions.cs b/src/Sentry.Bindings.Cocoa/ApiDefinitions.cs
index f33b1c6815..2c076ddf1a 100644
--- a/src/Sentry.Bindings.Cocoa/ApiDefinitions.cs
+++ b/src/Sentry.Bindings.Cocoa/ApiDefinitions.cs
@@ -416,9 +416,9 @@ interface SentryEnvelopeItemHeader : SentrySerializable
     [Export ("initWithType:length:filenname:contentType:")]
     NativeHandle Constructor (string type, nuint length, string filename, string contentType);
 
-    // -(instancetype _Nonnull)initWithType:(NSString * _Nonnull)type length:(NSUInteger)length contentType:(NSString * _Nonnull)contentType itemCount:(NSNumber * _Nonnull)itemCount;
+    // -(instancetype _Nonnull)initWithType:(NSString * _Nonnull)type length:(NSUInteger)length contentType:(NSString * _Nullable)contentType itemCount:(NSNumber * _Nonnull)itemCount;
     [Export ("initWithType:length:contentType:itemCount:")]
-    NativeHandle Constructor (string type, nuint length, string contentType, NSNumber itemCount);
+    NativeHandle Constructor (string type, nuint length, [NullAllowed] string contentType, NSNumber itemCount);
 
     // @property (readonly, copy, nonatomic) NSString * _Nonnull type;
     [Export ("type")]
diff --git a/src/Sentry.Bindings.Cocoa/Sentry.Bindings.Cocoa.csproj b/src/Sentry.Bindings.Cocoa/Sentry.Bindings.Cocoa.csproj
index 860b0f2db4..9ea684fbdb 100644
--- a/src/Sentry.Bindings.Cocoa/Sentry.Bindings.Cocoa.csproj
+++ b/src/Sentry.Bindings.Cocoa/Sentry.Bindings.Cocoa.csproj
@@ -102,7 +102,7 @@
 
   <!-- Choose between download and build -->
   <Target Name="_SetupCocoaSDK"
-          DependsOnTargets="_DownloadCocoaSDK;_BuildCocoaSDK"
+          DependsOnTargets="_DownloadCocoaSDK;_BuildCocoaSDK;_GenerateSentryCocoaBindings;SanitizeSentryCocoaFramework"
           Condition="$([MSBuild]::IsOSPlatform('OSX'))" />
 
   <!-- Setup exactly once: https://learn.microsoft.com/visualstudio/msbuild/run-target-exactly-once -->
@@ -122,7 +122,7 @@
   </Target>
 
   <!-- Generate bindings -->
-  <Target Name="_GenerateSentryCocoaBindings" AfterTargets="SetupCocoaSDK"
+  <Target Name="_GenerateSentryCocoaBindings"
           Condition="$([MSBuild]::IsOSPlatform('OSX'))"
           Inputs="$(SentryCocoaBindingInputs)"
           Outputs="ApiDefinitions.cs;StructsAndEnums.cs">
@@ -134,6 +134,13 @@
     <Exec Condition="'$(GITHUB_ACTIONS)' == 'true'" Command="pwsh ../../scripts/dirty-check.ps1 -PathToCheck $(MSBuildThisFileDirectory)" />
   </Target>
 
+  <!-- Sanitize the xcframework before NativeReference resolution and packing -->
+  <Target Name="SanitizeSentryCocoaFramework"
+          Condition="$([MSBuild]::IsOSPlatform('OSX')) and Exists('$(SentryCocoaFramework)')">
+    <Message Importance="High" Text="Sanitizing $(SentryCocoaFramework): removing dSYMs, Headers, Modules, PrivateHeaders (including symlinks)." />
+    <Exec Command="find &quot;$(SentryCocoaFramework)&quot; -depth \( -name dSYMs -o -name Headers -o -name Modules -o -name PrivateHeaders \) -exec echo Removing {} \; -exec rm -rf {} + 2&gt;/dev/null || true" />
+  </Target>
+
   <!-- Workaround for https://github.com/xamarin/xamarin-macios/issues/15299 -->
   <Target Name="_SetGeneratedSupportDelegatesInternal" BeforeTargets="CoreCompile" Condition="$([MSBuild]::IsOSPlatform('OSX'))"
     Inputs="$(GeneratedSourcesDir)SupportDelegates.g.cs" Outputs="$(GeneratedSourcesDir)SupportDelegates.g.cs.stamp">