diff --git a/lib/std/debug/SelfInfo.zig b/lib/std/debug/SelfInfo.zig
index 544cf0ac6ff4..7f07ea1e8b0e 100644
--- a/lib/std/debug/SelfInfo.zig
+++ b/lib/std/debug/SelfInfo.zig
@@ -1003,7 +1003,7 @@ fn readCoffDebugInfo(allocator: Allocator, coff_obj: *coff.Coff) !Module {
             di.dwarf = dwarf;
         }
 
-        const raw_path = try coff_obj.getPdbPath() orelse return di;
+        const raw_path = (coff_obj.getPdbPath() catch return error.InvalidDebugInfo) orelse return di;
         const path = blk: {
             if (fs.path.isAbsolute(raw_path)) {
                 break :blk raw_path;
diff --git a/lib/std/os/windows.zig b/lib/std/os/windows.zig
index ceed0618d1f1..d3123500219d 100644
--- a/lib/std/os/windows.zig
+++ b/lib/std/os/windows.zig
@@ -1292,6 +1292,18 @@ pub fn GetFinalPathNameByHandle(
             return final_path;
         },
         .Dos => {
+            // The "\??\" directory contains a bunch of symlinks that translates DOS volume names (like "C:")
+            // into NT volume names (like "\Device\HarddiskVolume2"). However, we want the DOS volume name, so
+            // we can just strip the "\??\" and return the subpath into that directory.
+            //
+            // Based on:
+            // - this stackoverflow post https://stackoverflow.com/questions/23041983/path-prefixes-and
+            // - downloading the WinObj program and inspecting the contents of "\??\"
+            const nt_device_alias_directory_prefix = std.unicode.utf8ToUtf16LeStringLiteral("\\??\\");
+            if (mem.startsWith(u16, final_path, nt_device_alias_directory_prefix)) {
+                return final_path[nt_device_alias_directory_prefix.len..];
+            }
+
             // parse the string to separate volume path from file path
             const expected_prefix = std.unicode.utf8ToUtf16LeStringLiteral("\\Device\\");