diff --git a/src/tools/tidy/src/allowed_run_make_makefiles.txt b/src/tools/tidy/src/allowed_run_make_makefiles.txt
index 33120cf93f903..c795ed7a76613 100644
--- a/src/tools/tidy/src/allowed_run_make_makefiles.txt
+++ b/src/tools/tidy/src/allowed_run_make_makefiles.txt
@@ -103,9 +103,7 @@ run-make/print-target-list/Makefile
 run-make/prune-link-args/Makefile
 run-make/raw-dylib-alt-calling-convention/Makefile
 run-make/raw-dylib-c/Makefile
-run-make/raw-dylib-custom-dlltool/Makefile
 run-make/raw-dylib-import-name-type/Makefile
-run-make/raw-dylib-inline-cross-dylib/Makefile
 run-make/raw-dylib-link-ordinal/Makefile
 run-make/raw-dylib-stdcall-ordinal/Makefile
 run-make/redundant-libs/Makefile
diff --git a/tests/run-make/raw-dylib-custom-dlltool/Makefile b/tests/run-make/raw-dylib-custom-dlltool/Makefile
deleted file mode 100644
index f5d5360a3fbe8..0000000000000
--- a/tests/run-make/raw-dylib-custom-dlltool/Makefile
+++ /dev/null
@@ -1,11 +0,0 @@
-# Test using -Cdlltool to change where raw-dylib looks for the dlltool binary.
-
-# only-windows
-# only-gnu
-# needs-dlltool
-
-include ../tools.mk
-
-all:
-	$(RUSTC) --crate-type lib --crate-name raw_dylib_test lib.rs -Cdlltool=$(CURDIR)/script.cmd
-	$(DIFF) output.txt "$(TMPDIR)"/output.txt
diff --git a/tests/run-make/raw-dylib-custom-dlltool/rmake.rs b/tests/run-make/raw-dylib-custom-dlltool/rmake.rs
new file mode 100644
index 0000000000000..86b952f0b4520
--- /dev/null
+++ b/tests/run-make/raw-dylib-custom-dlltool/rmake.rs
@@ -0,0 +1,24 @@
+// Instead of using the default dlltool, the rust compiler can also accept a custom
+// command file with the -C dlltool flag. This test uses it to compile some rust code
+// with the raw_dylib Windows-exclusive feature, and checks that the output contains
+// the string passed from the custom dlltool, confirming that the default dlltool was
+// successfully overridden.
+// See https://github.com/rust-lang/rust/pull/109677
+
+//@ only-windows
+//@ only-gnu
+//@ needs-dlltool
+// Reason: this test specifically checks the custom dlltool feature, only
+// available on Windows-gnu.
+
+use run_make_support::{diff, rustc};
+
+fn main() {
+    let out = rustc()
+        .crate_type("lib")
+        .crate_name("raw_dylib_test")
+        .input("lib.rs")
+        .arg("-Cdlltool=script.cmd")
+        .run();
+    diff().expected_file("output.txt").actual_file("actual.txt").normalize(r#"\r"#, "").run();
+}
diff --git a/tests/run-make/raw-dylib-custom-dlltool/script.cmd b/tests/run-make/raw-dylib-custom-dlltool/script.cmd
index 95f85c61c67d2..292c6aa706a26 100644
--- a/tests/run-make/raw-dylib-custom-dlltool/script.cmd
+++ b/tests/run-make/raw-dylib-custom-dlltool/script.cmd
@@ -1,2 +1,2 @@
-echo Called dlltool via script.cmd> %TMPDIR%\output.txt
+echo Called dlltool via script.cmd> %TMPDIR%\actual.txt
 dlltool.exe %*
diff --git a/tests/run-make/raw-dylib-inline-cross-dylib/Makefile b/tests/run-make/raw-dylib-inline-cross-dylib/Makefile
deleted file mode 100644
index 6b44b40e253e2..0000000000000
--- a/tests/run-make/raw-dylib-inline-cross-dylib/Makefile
+++ /dev/null
@@ -1,30 +0,0 @@
-# Regression test for calling an inline function that uses a raw-dylib function.
-
-# only-windows
-
-include ../tools.mk
-
-# We'd be using the llvm-objdump instead of the system objdump to ensure compatibility
-# with the LLVM bitcode generated by rustc but on Windows  piping/IO redirection under MSYS2 is wonky with llvm-objdump.
-OBJDUMP = objdump
-
-all:
-	$(RUSTC) --crate-type dylib --crate-name raw_dylib_test lib.rs -C prefer-dynamic
-	$(RUSTC) --crate-type dylib --crate-name raw_dylib_test_wrapper lib_wrapper.rs -C prefer-dynamic
-	$(RUSTC) --crate-type bin driver.rs -L "$(TMPDIR)" -C prefer-dynamic
-	# Make sure we don't find an import to the functions we expect to be inlined.
-	$(OBJDUMP) -p $(TMPDIR)/driver.exe | $(CGREP) -v -e "inline_library_function"
-	$(OBJDUMP) -p $(TMPDIR)/driver.exe | $(CGREP) -v -e "inline_library_function_calls_inline"
-	# Make sure we do find an import to the functions we expect to be imported.
-	$(OBJDUMP) -p $(TMPDIR)/driver.exe | $(CGREP) -e "library_function"
-	$(call COMPILE_OBJ,"$(TMPDIR)"/extern_1.obj,extern_1.c)
-	$(call COMPILE_OBJ,"$(TMPDIR)"/extern_2.obj,extern_2.c)
-ifdef IS_MSVC
-	$(CC) "$(TMPDIR)"/extern_1.obj -link -dll -out:"$(TMPDIR)"/extern_1.dll -noimplib
-	$(CC) "$(TMPDIR)"/extern_2.obj -link -dll -out:"$(TMPDIR)"/extern_2.dll -noimplib
-else
-	$(CC) "$(TMPDIR)"/extern_1.obj -shared -o "$(TMPDIR)"/extern_1.dll
-	$(CC) "$(TMPDIR)"/extern_2.obj -shared -o "$(TMPDIR)"/extern_2.dll
-endif
-	$(call RUN,driver) | tr -d '\r' > "$(TMPDIR)"/output.txt
-	$(RUSTC_TEST_OP) "$(TMPDIR)"/output.txt output.txt
diff --git a/tests/run-make/raw-dylib-inline-cross-dylib/rmake.rs b/tests/run-make/raw-dylib-inline-cross-dylib/rmake.rs
new file mode 100644
index 0000000000000..6e3b31a0cdbdc
--- /dev/null
+++ b/tests/run-make/raw-dylib-inline-cross-dylib/rmake.rs
@@ -0,0 +1,61 @@
+// When we generate the import library for a dylib or bin crate, we should generate it
+// for the symbols both for the current crate and all upstream crates. This allows for
+// using the link kind `raw-dylib` inside inline functions successfully. This test checks
+// that the import symbols in the object files match this convention, and that execution
+// of the binary results in all function names exported successfully.
+// See https://github.com/rust-lang/rust/pull/102988
+
+//@ only-windows
+
+use run_make_support::{cc, diff, is_msvc, llvm_objdump, run, rustc};
+
+fn main() {
+    rustc()
+        .crate_type("dylib")
+        .crate_name("raw_dylib_test")
+        .input("lib.rs")
+        .arg("-Cprefer-dynamic")
+        .run();
+    rustc()
+        .crate_type("dylib")
+        .crate_name("raw_dylib_test_wrapper")
+        .input("lib_wrapper.rs")
+        .arg("-Cprefer-dynamic")
+        .run();
+    rustc().crate_type("bin").input("driver.rs").arg("-Cprefer-dynamic").run();
+    llvm_objdump()
+        .arg("--private-headers")
+        .input("driver.exe")
+        .run()
+        // Make sure we don't find an import to the functions we expect to be inlined.
+        .assert_stdout_not_contains("inline_library_function")
+        // Make sure we do find an import to the functions we expect to be imported.
+        .assert_stdout_contains("library_function");
+    if is_msvc() {
+        cc().arg("-c").out_exe("extern_1").input("extern_1.c").run();
+        cc().arg("-c").out_exe("extern_2").input("extern_2.c").run();
+        cc().input("extern_1.obj")
+            .arg("-link")
+            .arg("-dll")
+            .arg("-out:extern_1.dll")
+            .arg("-noimplib")
+            .run();
+        cc().input("extern_2.obj")
+            .arg("-link")
+            .arg("-dll")
+            .arg("-out:extern_2.dll")
+            .arg("-noimplib")
+            .run();
+    } else {
+        cc().arg("-v").arg("-c").out_exe("extern_1").input("extern_1.c").run();
+        cc().arg("-v").arg("-c").out_exe("extern_2").input("extern_2.c").run();
+        cc().input("extern_1").out_exe("extern_1.dll").arg("-shared").run();
+        cc().input("extern_2").out_exe("extern_2.dll").arg("-shared").run();
+    }
+    let out = run("driver").stdout_utf8();
+    diff()
+        .expected_file("output.txt")
+        .actual_text("actual_output", out)
+        .normalize(r#"\r"#, "")
+        .run();
+}