diff --git a/src/resolver/resolve_path.zig b/src/resolver/resolve_path.zig
index 151cf1ec2f719..466333a9828e8 100644
--- a/src/resolver/resolve_path.zig
+++ b/src/resolver/resolve_path.zig
@@ -1842,7 +1842,7 @@ pub const PosixToWinNormalizer = struct {
 
     // underlying implementation:
 
-    fn resolveWithExternalBuf(
+    pub fn resolveWithExternalBuf(
         buf: *Buf,
         source_dir: []const u8,
         maybe_posix_path: []const u8,
@@ -1856,11 +1856,16 @@ pub const PosixToWinNormalizer = struct {
                     const source_root = windowsFilesystemRoot(source_dir);
                     @memcpy(buf[0..source_root.len], source_root);
                     @memcpy(buf[source_root.len..][0 .. maybe_posix_path.len - 1], maybe_posix_path[1..]);
-                    const res = buf[0 .. source_root.len + maybe_posix_path.len - 1];
+                    buf[source_root.len + maybe_posix_path.len - 1] = 0;
+                    const res = buf[0 .. source_root.len + maybe_posix_path.len - 1 :0];
                     assert(!bun.strings.isWindowsAbsolutePathMissingDriveLetter(u8, res));
-                    return res;
+                    return ensureLongPath(buf, res);
                 }
             }
+
+            @memcpy(buf.ptr, maybe_posix_path);
+            buf[maybe_posix_path.len] = 0;
+            return ensureLongPath(buf, buf[0..maybe_posix_path.len :0]);
         }
         return maybe_posix_path;
     }
@@ -1881,11 +1886,16 @@ pub const PosixToWinNormalizer = struct {
                     const source_root = windowsFilesystemRoot(cwd);
                     assert(source_root.ptr == source_root.ptr);
                     @memcpy(buf[source_root.len..][0 .. maybe_posix_path.len - 1], maybe_posix_path[1..]);
-                    const res = buf[0 .. source_root.len + maybe_posix_path.len - 1];
+                    buf[source_root.len + maybe_posix_path.len - 1] = 0;
+                    const res = buf[0 .. source_root.len + maybe_posix_path.len - 1 :0];
                     assert(!bun.strings.isWindowsAbsolutePathMissingDriveLetter(u8, res));
-                    return res;
+                    return ensureLongPath(buf, res);
                 }
             }
+
+            @memcpy(buf.ptr, maybe_posix_path);
+            buf[maybe_posix_path.len] = 0;
+            return ensureLongPath(buf, buf[0..maybe_posix_path.len :0]);
         }
 
         return maybe_posix_path;
@@ -1910,15 +1920,47 @@ pub const PosixToWinNormalizer = struct {
                     buf[source_root.len + maybe_posix_path.len - 1] = 0;
                     const res = buf[0 .. source_root.len + maybe_posix_path.len - 1 :0];
                     assert(!bun.strings.isWindowsAbsolutePathMissingDriveLetter(u8, res));
-                    return res;
+                    return ensureLongPath(buf, res);
                 }
             }
+
+            @memcpy(buf.ptr, maybe_posix_path);
+            buf[maybe_posix_path.len] = 0;
+            return ensureLongPath(buf, buf[0..maybe_posix_path.len :0]);
         }
 
         @memcpy(buf.ptr, maybe_posix_path);
         buf[maybe_posix_path.len] = 0;
         return buf[0..maybe_posix_path.len :0];
     }
+
+    /// `res` needs to exist in `buf` and needs to start at the beginning
+    pub fn ensureLongPath(buf: anytype, res: [:0]const u8) [:0]u8 {
+        assert(buf.ptr == res.ptr);
+        if (bun.Environment.isWindows) {
+            const long_path_len = bun.windows.GetLongPathNameA(
+                @ptrCast(buf.ptr),
+                // it's safe to use the same buffer
+                @ptrCast(buf.ptr),
+                @intCast(buf.len),
+            );
+
+            if (long_path_len == 0) {
+                // Length 0 means there was an error. This could happen
+                // if the file/dir does not exist, or permissions are missing
+                // for any component in the path. In this case, ignore the
+                // error and return the normalized path.
+                //
+                // If it doesn't exist, but the 8.3 path does, it will resolve
+                // correctly because the dir cache will cache it.
+                return buf[0..res.len :0];
+            }
+
+            return buf[0..long_path_len :0];
+        }
+
+        return buf[0..res.len :0];
+    }
 };
 
 /// Used in PathInlines.h
diff --git a/src/resolver/resolver.zig b/src/resolver/resolver.zig
index 34dec389f1c38..b29a102a6d772 100644
--- a/src/resolver/resolver.zig
+++ b/src/resolver/resolver.zig
@@ -1160,8 +1160,11 @@ pub const Resolver = struct {
         // Treating these paths as absolute paths on all platforms means Windows
         // users will not be able to accidentally make use of these paths.
         if (std.fs.path.isAbsolute(import_path)) {
+            var normalizer = ResolvePath.PosixToWinNormalizer{};
+            const abs_import_path = normalizer.resolve(source_dir, import_path);
+
             if (r.debug_logs) |*debug| {
-                debug.addNoteFmt("The import \"{s}\" is being treated as an absolute path", .{import_path});
+                debug.addNoteFmt("The import \"{s}\" is being treated as an absolute path", .{abs_import_path});
             }
 
             // First, check path overrides from the nearest enclosing TypeScript "tsconfig.json" file
@@ -1169,7 +1172,7 @@ pub const Resolver = struct {
                 const dir_info: *DirInfo = _dir_info;
                 if (dir_info.enclosing_tsconfig_json) |tsconfig| {
                     if (tsconfig.paths.count() > 0) {
-                        if (r.matchTSConfigPaths(tsconfig, import_path, kind)) |res| {
+                        if (r.matchTSConfigPaths(tsconfig, abs_import_path, kind)) |res| {
 
                             // We don't set the directory fd here because it might remap an entirely different directory
                             return .{
@@ -1187,26 +1190,25 @@ pub const Resolver = struct {
                 }
             }
 
-            if (r.opts.external.abs_paths.count() > 0 and r.opts.external.abs_paths.contains(import_path)) {
+            if (r.opts.external.abs_paths.count() > 0 and r.opts.external.abs_paths.contains(abs_import_path)) {
                 // If the string literal in the source text is an absolute path and has
                 // been marked as an external module, mark it as *not* an absolute path.
                 // That way we preserve the literal text in the output and don't generate
                 // a relative path from the output directory to that path.
                 if (r.debug_logs) |*debug| {
-                    debug.addNoteFmt("The path \"{s}\" is marked as external by the user", .{import_path});
+                    debug.addNoteFmt("The path \"{s}\" is marked as external by the user", .{abs_import_path});
                 }
 
                 return .{
                     .success = Result{
-                        .path_pair = .{ .primary = Path.init(import_path) },
+                        .path_pair = .{ .primary = Path.init(abs_import_path) },
                         .is_external = true,
                     },
                 };
             }
 
             // Run node's resolution rules (e.g. adding ".js")
-            var normalizer = ResolvePath.PosixToWinNormalizer{};
-            if (r.loadAsFileOrDirectory(normalizer.resolve(source_dir, import_path), kind)) |entry| {
+            if (r.loadAsFileOrDirectory(abs_import_path, kind)) |entry| {
                 return .{
                     .success = Result{
                         .dirname_fd = entry.dirname_fd,
@@ -1230,7 +1232,10 @@ pub const Resolver = struct {
 
         if (check_relative) {
             const parts = [_]string{ source_dir, import_path };
-            const abs_path = r.fs.absBuf(&parts, bufs(.relative_abs_path));
+            const joined = r.fs.absBufZ(&parts, bufs(.relative_abs_path));
+            const abs_path: []u8 = ResolvePath.PosixToWinNormalizer.ensureLongPath(bufs(.relative_abs_path), joined);
+            // var normalizer = ResolvePath.PosixToWinNormalizer{};
+            // const abs_path = normalizer.resolve(source_dir, joined);
 
             if (r.opts.external.abs_paths.count() > 0 and r.opts.external.abs_paths.contains(abs_path)) {
                 // If the string literal in the source text is an absolute path and has
@@ -2437,7 +2442,9 @@ pub const Resolver = struct {
             return r.loadNodeModules(import_path, kind, source_dir_info, global_cache, false);
         } else {
             const paths = [_]string{ source_dir_info.abs_path, import_path };
-            const resolved = r.fs.absBuf(&paths, bufs(.resolve_without_remapping));
+            const joined = r.fs.absBuf(&paths, bufs(.resolve_without_remapping));
+            var normalizer = ResolvePath.PosixToWinNormalizer{};
+            const resolved = normalizer.resolve(source_dir_info.abs_path, joined);
             if (r.loadAsFileOrDirectory(resolved, kind)) |result| {
                 return .{ .success = result };
             }
diff --git a/src/windows.zig b/src/windows.zig
index 902110d7189b0..58e9d05e97860 100644
--- a/src/windows.zig
+++ b/src/windows.zig
@@ -3405,6 +3405,18 @@ pub extern "kernel32" fn GetThreadDescription(
     *PWSTR, // [out]
 ) std.os.windows.HRESULT;
 
+pub extern "kernel32" fn GetLongPathNameW(
+    lpszShortPath: LPCWSTR,
+    lpszLongPath: LPWSTR,
+    cchBuffer: DWORD,
+) DWORD;
+
+pub extern "kernel32" fn GetLongPathNameA(
+    lpszShortPath: LPCSTR,
+    lpszLongPath: LPSTR,
+    cchBuffer: DWORD,
+) DWORD;
+
 pub const ENABLE_VIRTUAL_TERMINAL_INPUT = 0x200;
 pub const ENABLE_WRAP_AT_EOL_OUTPUT = 0x0002;
 pub const ENABLE_PROCESSED_OUTPUT = 0x0001;
diff --git a/test/bundler/fixtures/with-assets/img.png b/test/bundler/fixtures/with-assets/img.png
index 7c48c8d6a027c..0dd1608e45a9c 120000
Binary files a/test/bundler/fixtures/with-assets/img.png and b/test/bundler/fixtures/with-assets/img.png differ
diff --git a/test/js/bun/resolve/longjavascriptfilename.js b/test/js/bun/resolve/longjavascriptfilename.js
new file mode 100644
index 0000000000000..bbf2a2836f33d
--- /dev/null
+++ b/test/js/bun/resolve/longjavascriptfilename.js
@@ -0,0 +1 @@
+module.exports.foo = "bar";
diff --git a/test/js/bun/resolve/resolve.test.ts b/test/js/bun/resolve/resolve.test.ts
index 1a46b049cdabb..bd6225dbd3e04 100644
--- a/test/js/bun/resolve/resolve.test.ts
+++ b/test/js/bun/resolve/resolve.test.ts
@@ -312,3 +312,7 @@ it.todo("import override to bun:test", async () => {
   // @ts-expect-error
   expect(await import("#bun_test")).toBeDefined();
 });
+
+it("should import short paths", () => {
+  expect(require("./LONGJA~1.JS")).toBeDefined();
+});