diff --git a/apple-codesign/CHANGELOG.md b/apple-codesign/CHANGELOG.md
index 153953d2f..236a073f4 100644
--- a/apple-codesign/CHANGELOG.md
+++ b/apple-codesign/CHANGELOG.md
@@ -62,6 +62,8 @@ Released on ReleaseDate.
 * Bundle signing logic has been significantly overhauled to hopefully make
   it conform with Apple tooling's behavior. This likely fixed several bugs
   with bundle signing.
+* Fixed a bundle signing bug where overwriting symlinks would incorrectly
+  result in an `Error: I/O error: File exists (os error 17)` or similar.
 * aws crates 0.53 -> 0.57.
 * bitflags 1.3 -> 2.0.
 * cryptographic-message-syntax 0.19 -> 0.25.
diff --git a/apple-codesign/src/bundle_signing.rs b/apple-codesign/src/bundle_signing.rs
index e1020f43b..48170b1cb 100644
--- a/apple-codesign/src/bundle_signing.rs
+++ b/apple-codesign/src/bundle_signing.rs
@@ -303,6 +303,13 @@ impl<'a, 'key> BundleFileHandler for SingleBundleHandler<'a, 'key> {
         let dest_path = self.dest_dir.join(dest_rel_path);
 
         if source_path != dest_path {
+            // Remove an existing file before installing the replacement. In
+            // the case of symlinks this is required due to how symlink creation
+            // works.
+            if dest_path.symlink_metadata().is_ok() {
+                std::fs::remove_file(&dest_path)?;
+            }
+
             if let Some(parent) = dest_path.parent() {
                 std::fs::create_dir_all(parent)?;
             }
diff --git a/apple-codesign/tests/cmd/sign-bundle-symlink-overwrite.trycmd b/apple-codesign/tests/cmd/sign-bundle-symlink-overwrite.trycmd
index 672c567e1..60b7f1137 100644
--- a/apple-codesign/tests/cmd/sign-bundle-symlink-overwrite.trycmd
+++ b/apple-codesign/tests/cmd/sign-bundle-symlink-overwrite.trycmd
@@ -40,7 +40,6 @@ writing signed main executable to MyApp.app.signed/Contents/MacOS/MyApp
 $ ln -sf file-01.txt MyApp.app/Contents/Resources/file.txt
 
 $ rcodesign sign MyApp.app MyApp.app.signed
-? 1
 signing MyApp.app to MyApp.app.signed
 signing bundle at MyApp.app
 signing 0 nested bundles in the following order:
@@ -53,6 +52,15 @@ sealing regular file Resources/file-01.txt
 copying file MyApp.app/Contents/Resources/file-01.txt -> MyApp.app.signed/Contents/Resources/file-01.txt
 sealing symlink Resources/file.txt -> file-01.txt
 replicating symlink MyApp.app.signed/Contents/Resources/file.txt -> file-01.txt
-Error: I/O error: File exists (os error 17)
+writing sealed resources to MyApp.app.signed/Contents/_CodeSignature/CodeResources
+signing main executable Contents/MacOS/MyApp
+setting main executable binary identifier to com.example.mybundle (derived from CFBundleIdentifier in Info.plist)
+inferring default signing settings from Mach-O binary
+signing Mach-O binary at index 0
+binary targets macOS >= 11.0.0 with SDK 11.0.0
+creating ad-hoc signature
+code directory version: 132096
+total signature size: 421 bytes
+writing signed main executable to MyApp.app.signed/Contents/MacOS/MyApp
 
 ```