diff --git a/compiler/rustc_builtin_macros/src/source_util.rs b/compiler/rustc_builtin_macros/src/source_util.rs
index f53574601441..16003c8ba135 100644
--- a/compiler/rustc_builtin_macros/src/source_util.rs
+++ b/compiler/rustc_builtin_macros/src/source_util.rs
@@ -275,7 +275,15 @@ fn load_binary_file(
         }
     };
     match cx.source_map().load_binary_file(&resolved_path) {
-        Ok(data) => Ok(data),
+        Ok(data) => {
+            cx.sess
+                .psess
+                .file_depinfo
+                .borrow_mut()
+                .insert(Symbol::intern(&resolved_path.to_string_lossy()));
+
+            Ok(data)
+        }
         Err(io_err) => {
             let mut err = cx.dcx().struct_span_err(
                 macro_span,
diff --git a/compiler/rustc_interface/src/passes.rs b/compiler/rustc_interface/src/passes.rs
index 60b45f7391b5..f5fb8031ab0f 100644
--- a/compiler/rustc_interface/src/passes.rs
+++ b/compiler/rustc_interface/src/passes.rs
@@ -9,6 +9,7 @@ use rustc_ast::{self as ast, CRATE_NODE_ID};
 use rustc_attr_parsing::{AttributeParser, Early, ShouldEmit};
 use rustc_codegen_ssa::traits::CodegenBackend;
 use rustc_codegen_ssa::{CodegenResults, CrateInfo};
+use rustc_data_structures::indexmap::IndexMap;
 use rustc_data_structures::jobserver::Proxy;
 use rustc_data_structures::steal::Steal;
 use rustc_data_structures::sync::{AppendOnlyIndexVec, FreezeLock, WorkerLocal};
@@ -584,7 +585,7 @@ fn write_out_deps(tcx: TyCtxt<'_>, outputs: &OutputFilenames, out_filenames: &[P
     let result: io::Result<()> = try {
         // Build a list of files used to compile the output and
         // write Makefile-compatible dependency rules
-        let mut files: Vec<(String, u64, Option<SourceFileHash>)> = sess
+        let mut files: IndexMap<String, (u64, Option<SourceFileHash>)> = sess
             .source_map()
             .files()
             .iter()
@@ -593,10 +594,12 @@ fn write_out_deps(tcx: TyCtxt<'_>, outputs: &OutputFilenames, out_filenames: &[P
             .map(|fmap| {
                 (
                     escape_dep_filename(&fmap.name.prefer_local_unconditionally().to_string()),
-                    // This needs to be unnormalized,
-                    // as external tools wouldn't know how rustc normalizes them
-                    fmap.unnormalized_source_len as u64,
-                    fmap.checksum_hash,
+                    (
+                        // This needs to be unnormalized,
+                        // as external tools wouldn't know how rustc normalizes them
+                        fmap.unnormalized_source_len as u64,
+                        fmap.checksum_hash,
+                    ),
                 )
             })
             .collect();
@@ -614,7 +617,7 @@ fn write_out_deps(tcx: TyCtxt<'_>, outputs: &OutputFilenames, out_filenames: &[P
         fn hash_iter_files<P: AsRef<Path>>(
             it: impl Iterator<Item = P>,
             checksum_hash_algo: Option<SourceFileHashAlgorithm>,
-        ) -> impl Iterator<Item = (P, u64, Option<SourceFileHash>)> {
+        ) -> impl Iterator<Item = (P, (u64, Option<SourceFileHash>))> {
             it.map(move |path| {
                 match checksum_hash_algo.and_then(|algo| {
                     fs::File::open(path.as_ref())
@@ -630,8 +633,8 @@ fn write_out_deps(tcx: TyCtxt<'_>, outputs: &OutputFilenames, out_filenames: &[P
                         })
                         .ok()
                 }) {
-                    Some((file_len, checksum)) => (path, file_len, Some(checksum)),
-                    None => (path, 0, None),
+                    Some((file_len, checksum)) => (path, (file_len, Some(checksum))),
+                    None => (path, (0, None)),
                 }
             })
         }
@@ -705,18 +708,14 @@ fn write_out_deps(tcx: TyCtxt<'_>, outputs: &OutputFilenames, out_filenames: &[P
                     file,
                     "{}: {}\n",
                     path.display(),
-                    files
-                        .iter()
-                        .map(|(path, _file_len, _checksum_hash_algo)| path.as_str())
-                        .intersperse(" ")
-                        .collect::<String>()
+                    files.keys().map(String::as_str).intersperse(" ").collect::<String>()
                 )?;
             }
 
             // Emit a fake target for each input file to the compilation. This
             // prevents `make` from spitting out an error if a file is later
             // deleted. For more info see #28735
-            for (path, _file_len, _checksum_hash_algo) in &files {
+            for path in files.keys() {
                 writeln!(file, "{path}:")?;
             }
 
@@ -745,7 +744,7 @@ fn write_out_deps(tcx: TyCtxt<'_>, outputs: &OutputFilenames, out_filenames: &[P
             if sess.opts.unstable_opts.checksum_hash_algorithm().is_some() {
                 files
                     .iter()
-                    .filter_map(|(path, file_len, hash_algo)| {
+                    .filter_map(|(path, (file_len, hash_algo))| {
                         hash_algo.map(|hash_algo| (path, file_len, hash_algo))
                     })
                     .try_for_each(|(path, file_len, checksum_hash)| {
diff --git a/tests/run-make/checksum-freshness/binary_file b/tests/run-make/checksum-freshness/binary_file
new file mode 100644
index 000000000000..45f1873fb781
--- /dev/null
+++ b/tests/run-make/checksum-freshness/binary_file
@@ -0,0 +1 @@
+binary˙
\ No newline at end of file
diff --git a/tests/run-make/checksum-freshness/expected.d b/tests/run-make/checksum-freshness/expected.d
index 51467af53a20..4554c509e36e 100644
--- a/tests/run-make/checksum-freshness/expected.d
+++ b/tests/run-make/checksum-freshness/expected.d
@@ -1,6 +1,8 @@
-lib.d: lib.rs foo.rs
+lib.d: lib.rs foo.rs binary_file
 
 lib.rs:
 foo.rs:
-# checksum:blake3=94af75ee4ed805434484c3de51c9025278e5c3ada2315e2592052e102168a503 file_len:120 lib.rs
+binary_file:
+# checksum:blake3=4ac56f3f877798fb762d714c7bcb72e70133f4cc585f80dbd99c07755ae2c7f6 file_len:222 lib.rs
 # checksum:blake3=2720e17bfda4f3b2a5c96bb61b7e76ed8ebe3359b34128c0e5d8032c090a4f1a file_len:119 foo.rs
+# checksum:blake3=119a5db8711914922c5b1c1908be4958175c5afa95c08888de594725329b5439 file_len:7 binary_file
diff --git a/tests/run-make/checksum-freshness/lib.rs b/tests/run-make/checksum-freshness/lib.rs
index 7bc6757959b1..0cd4243423de 100644
--- a/tests/run-make/checksum-freshness/lib.rs
+++ b/tests/run-make/checksum-freshness/lib.rs
@@ -1,7 +1,8 @@
 // A basic library to be used in tests with no real purpose.
 
 mod foo;
-
+// Binary file with invalid UTF-8 sequence.
+static BINARY_FILE: &[u8] = include_bytes!("binary_file");
 pub fn sum(a: i32, b: i32) -> i32 {
     a + b
 }