diff --git a/src/cargo/core/compiler/context/compilation_files.rs b/src/cargo/core/compiler/context/compilation_files.rs
index 04d75fe0ac5..5d2cf4efce9 100644
--- a/src/cargo/core/compiler/context/compilation_files.rs
+++ b/src/cargo/core/compiler/context/compilation_files.rs
@@ -608,6 +608,12 @@ fn should_use_metadata(bcx: &BuildContext<'_, '_>, unit: &Unit) -> bool {
     // - wasm32 executables: When using emscripten, the path to the .wasm file
     //   is embedded in the .js file, so we don't want the hash in there.
     //   TODO: Is this necessary for wasm32-unknown-unknown?
+    // - apple executables: The executable name is used in the dSYM directory
+    //   (such as `target/debug/foo.dSYM/Contents/Resources/DWARF/foo-64db4e4bf99c12dd`).
+    //   Unfortunately this causes problems with our current backtrace
+    //   implementation which looks for a file matching the exe name exactly.
+    //   See https://github.com/rust-lang/rust/issues/72550#issuecomment-638501691
+    //   for more details.
     //
     // This is only done for local packages, as we don't expect to export
     // dependencies.
@@ -622,7 +628,8 @@ fn should_use_metadata(bcx: &BuildContext<'_, '_>, unit: &Unit) -> bool {
     if (unit.target.is_dylib()
         || unit.target.is_cdylib()
         || (unit.target.is_executable() && short_name.starts_with("wasm32-"))
-        || (unit.target.is_executable() && short_name.contains("msvc")))
+        || (unit.target.is_executable() && short_name.contains("msvc"))
+        || (unit.target.is_executable() && short_name.contains("-apple-")))
         && unit.pkg.package_id().source_id().is_path()
         && env::var("__CARGO_DEFAULT_LIB_METADATA").is_err()
     {
diff --git a/src/cargo/core/compiler/fingerprint.rs b/src/cargo/core/compiler/fingerprint.rs
index 145a622bb1f..b432839850a 100644
--- a/src/cargo/core/compiler/fingerprint.rs
+++ b/src/cargo/core/compiler/fingerprint.rs
@@ -1229,7 +1229,7 @@ fn calculate_normal(cx: &mut Context<'_, '_>, unit: &Unit) -> CargoResult<Finger
     let outputs = cx
         .outputs(unit)?
         .iter()
-        .filter(|output| output.flavor != FileFlavor::DebugInfo)
+        .filter(|output| !matches!(output.flavor, FileFlavor::DebugInfo | FileFlavor::Auxiliary))
         .map(|output| output.path.clone())
         .collect();
 
diff --git a/tests/testsuite/build.rs b/tests/testsuite/build.rs
index 204d23cef0e..f176e77a19e 100644
--- a/tests/testsuite/build.rs
+++ b/tests/testsuite/build.rs
@@ -4149,7 +4149,7 @@ fn uplift_dsym_of_bin_on_mac() {
     assert!(p.target_debug_dir().join("foo.dSYM").is_dir());
     assert!(p.target_debug_dir().join("b.dSYM").is_dir());
     assert!(p.target_debug_dir().join("b.dSYM").is_symlink());
-    assert!(p.target_debug_dir().join("examples/c.dSYM").is_symlink());
+    assert!(p.target_debug_dir().join("examples/c.dSYM").is_dir());
     assert!(!p.target_debug_dir().join("c.dSYM").exists());
     assert!(!p.target_debug_dir().join("d.dSYM").exists());
 }
diff --git a/tests/testsuite/collisions.rs b/tests/testsuite/collisions.rs
index e81ef90919f..5b94aae28ec 100644
--- a/tests/testsuite/collisions.rs
+++ b/tests/testsuite/collisions.rs
@@ -91,9 +91,9 @@ This may become a hard error in the future; see <https://github.com/rust-lang/ca
 }
 
 #[cargo_test]
-// --out-dir and examples are currently broken on MSVC.
+// --out-dir and examples are currently broken on MSVC and apple.
 // See https://github.com/rust-lang/cargo/issues/7493
-#[cfg(not(target_env = "msvc"))]
+#[cfg_attr(any(target_env = "msvc", target_vendor = "apple"), ignore)]
 fn collision_export() {
     // `--out-dir` combines some things which can cause conflicts.
     let p = project()
diff --git a/tests/testsuite/freshness.rs b/tests/testsuite/freshness.rs
index 62059734c74..9d9069cc849 100644
--- a/tests/testsuite/freshness.rs
+++ b/tests/testsuite/freshness.rs
@@ -491,8 +491,8 @@ fn changing_bin_features_caches_targets() {
     /* Targets should be cached from the first build */
 
     let mut e = p.cargo("build");
-    // MSVC does not include hash in binary filename, so it gets recompiled.
-    if cfg!(target_env = "msvc") {
+    // MSVC/apple does not include hash in binary filename, so it gets recompiled.
+    if cfg!(any(target_env = "msvc", target_vendor = "apple")) {
         e.with_stderr("[COMPILING] foo[..]\n[FINISHED] dev[..]");
     } else {
         e.with_stderr("[FINISHED] dev[..]");
@@ -501,7 +501,7 @@ fn changing_bin_features_caches_targets() {
     p.rename_run("foo", "off2").with_stdout("feature off").run();
 
     let mut e = p.cargo("build --features foo");
-    if cfg!(target_env = "msvc") {
+    if cfg!(any(target_env = "msvc", target_vendor = "apple")) {
         e.with_stderr("[COMPILING] foo[..]\n[FINISHED] dev[..]");
     } else {
         e.with_stderr("[FINISHED] dev[..]");
@@ -2436,3 +2436,39 @@ fn linking_interrupted() {
         )
         .run();
 }
+
+#[cargo_test]
+#[cfg_attr(
+    not(all(target_arch = "x86_64", target_os = "windows", target_env = "msvc")),
+    ignore
+)]
+fn lld_is_fresh() {
+    // Check for bug when using lld linker that it remains fresh with dylib.
+    let p = project()
+        .file(
+            ".cargo/config",
+            r#"
+                [target.x86_64-pc-windows-msvc]
+                linker = "rust-lld"
+                rustflags = ["-C", "link-arg=-fuse-ld=lld"]
+            "#,
+        )
+        .file(
+            "Cargo.toml",
+            r#"
+                [package]
+                name = "foo"
+                version = "0.1.0"
+
+                [lib]
+                crate-type = ["dylib"]
+            "#,
+        )
+        .file("src/lib.rs", "")
+        .build();
+
+    p.cargo("build").run();
+    p.cargo("build -v")
+        .with_stderr("[FRESH] foo [..]\n[FINISHED] [..]")
+        .run();
+}