diff --git a/compiler/rustc_codegen_llvm/src/debuginfo/metadata.rs b/compiler/rustc_codegen_llvm/src/debuginfo/metadata.rs
index cf78fc56b498c..99907dbc41a7c 100644
--- a/compiler/rustc_codegen_llvm/src/debuginfo/metadata.rs
+++ b/compiler/rustc_codegen_llvm/src/debuginfo/metadata.rs
@@ -851,9 +851,22 @@ pub fn build_compile_unit_di_node<'ll, 'tcx>(
     // FIXME(#41252) Remove "clang LLVM" if we can get GDB and LLVM to play nice.
     let producer = format!("clang LLVM ({rustc_producer})");
 
-    use rustc_session::RemapFileNameExt;
     let name_in_debuginfo = name_in_debuginfo.to_string_lossy();
-    let work_dir = tcx.sess.opts.working_dir.for_codegen(tcx.sess).to_string_lossy();
+    debug!(?name_in_debuginfo, "build_compile_unit_di_node");
+
+    // Path of working directory in the root DI node seems to be embedded in
+    // executables. Hence, we trim them when the scope of `unsplit-debuginfo`
+    // is present, as if it is kinda a "unsplit" debuginfo.
+    use rustc_session::config::RemapPathScopeComponents;
+    use rustc_session::RemapFileNameExt;
+    let work_dir = tcx
+        .sess
+        .opts
+        .working_dir
+        .for_scope(tcx.sess, RemapPathScopeComponents::UNSPLIT_DEBUGINFO)
+        .to_string_lossy();
+    debug!(?work_dir, "build_compile_unit_di_node");
+
     let flags = "\0";
     let output_filenames = tcx.output_filenames(());
     let split_name = if tcx.sess.target_can_use_split_dwarf() {
diff --git a/tests/run-make/split-debuginfo/Makefile b/tests/run-make/split-debuginfo/Makefile
index d417fd147bff0..9338d658c5084 100644
--- a/tests/run-make/split-debuginfo/Makefile
+++ b/tests/run-make/split-debuginfo/Makefile
@@ -28,7 +28,7 @@ packed-remapped-scope:
 	[ -d $(TMPDIR)/foo.dSYM ]
 	# As of 2023-12, `OSO` should be the only thing that cannot be trimmed. See rust-lang/rust#116948
 	dsymutil -s $(TMPDIR)/foo | grep $(TMPDIR) || exit 1 # expected: `grep $(TMPDIR)` to exit 1
-	dsymutil -s $(TMPDIR)/foo | grep $(HERE) || exit 1 # expected: `grep $(HERE)` to exit 1
+	dsymutil -s $(TMPDIR)/foo | (! grep $(HERE)) || exit 1
 	rm -rf $(TMPDIR)/foo.dSYM
 	rm $(TMPDIR)/$(call BIN,foo)
 
@@ -64,7 +64,7 @@ unpacked-remapped-scope:
 	[ ! -d $(TMPDIR)/foo.dSYM ]
 	# As of 2023-12, `OSO` should be the only thing that cannot be trimmed. See rust-lang/rust#116948
 	dsymutil -s $(TMPDIR)/foo | grep $(TMPDIR) || exit 1 # expected: `grep $(TMPDIR)` to exit 1
-	dsymutil -s $(TMPDIR)/foo | grep $(HERE) || exit 1 # expected: `grep $(HERE)` to exit 1
+	dsymutil -s $(TMPDIR)/foo | (! grep $(HERE)) || exit 1
 	rm $(TMPDIR)/*.o
 	rm $(TMPDIR)/$(call BIN,foo)
 
@@ -210,7 +210,7 @@ packed-remapped-scope:
 		--remap-path-prefix $(HERE)=/b \
 		-Z remap-path-scope=object foo.rs -g
 	readelf -wi $(TMPDIR)/foo | (! grep $(TMPDIR)) || exit 1
-	readelf -wi $(TMPDIR)/foo | grep $(HERE) || exit 1 # expected: `grep $(HERE)` to exit 1
+	readelf -wi $(TMPDIR)/foo | (! grep $(HERE)) || exit 1
 	ls $(TMPDIR)/*.o && exit 1 || exit 0
 	ls $(TMPDIR)/*.dwo && exit 1 || exit 0
 	rm $(TMPDIR)/foo.dwp
@@ -380,7 +380,7 @@ unpacked-remapped-scope:
 		--remap-path-prefix $(HERE)=/b \
 		-Z remap-path-scope=object foo.rs -g
 	readelf -wi $(TMPDIR)/foo | (! grep $(TMPDIR)) || exit 1
-	readelf -wi $(TMPDIR)/foo | grep $(HERE) || exit 1 # expected: `grep $(HERE)` to exit 1
+	readelf -wi $(TMPDIR)/foo | (! grep $(HERE)) || exit 1
 	rm $(TMPDIR)/*.o
 	ls $(TMPDIR)/*.dwo && exit 1 || exit 0
 	ls $(TMPDIR)/*.dwp && exit 1 || exit 0