diff --git a/src/compiler/crystal/codegen/link.cr b/src/compiler/crystal/codegen/link.cr
index 33248e93e19b..b2b827916cbf 100644
--- a/src/compiler/crystal/codegen/link.cr
+++ b/src/compiler/crystal/codegen/link.cr
@@ -120,18 +120,18 @@ module Crystal
   end
 
   class Program
-    def lib_flags
-      has_flag?("msvc") ? lib_flags_windows : lib_flags_posix
+    def lib_flags(cross_compiling : Bool = false)
+      has_flag?("msvc") ? lib_flags_windows(cross_compiling) : lib_flags_posix(cross_compiling)
     end
 
-    private def lib_flags_windows
+    private def lib_flags_windows(cross_compiling)
       flags = [] of String
 
       # Add CRYSTAL_LIBRARY_PATH locations, so the linker preferentially
       # searches user-given library paths.
       if has_flag?("msvc")
         CrystalLibraryPath.paths.each do |path|
-          flags << Process.quote_windows("/LIBPATH:#{path}")
+          flags << quote_flag("/LIBPATH:#{path}", cross_compiling)
         end
       end
 
@@ -141,14 +141,14 @@ module Crystal
         end
 
         if libname = ann.lib
-          flags << Process.quote_windows("#{libname}.lib")
+          flags << quote_flag("#{libname}.lib", cross_compiling)
         end
       end
 
       flags.join(" ")
     end
 
-    private def lib_flags_posix
+    private def lib_flags_posix(cross_compiling)
       flags = [] of String
       static_build = has_flag?("static")
 
@@ -158,7 +158,7 @@ module Crystal
       # Add CRYSTAL_LIBRARY_PATH locations, so the linker preferentially
       # searches user-given library paths.
       CrystalLibraryPath.paths.each do |path|
-        flags << Process.quote_posix("-L#{path}")
+        flags << quote_flag("-L#{path}", cross_compiling)
       end
 
       link_annotations.reverse_each do |ann|
@@ -173,17 +173,25 @@ module Crystal
         elsif (lib_name = ann.lib) && (flag = pkg_config(lib_name, static_build))
           flags << flag
         elsif (lib_name = ann.lib)
-          flags << Process.quote_posix("-l#{lib_name}")
+          flags << quote_flag("-l#{lib_name}", cross_compiling)
         end
 
         if framework = ann.framework
-          flags << "-framework" << Process.quote_posix(framework)
+          flags << "-framework" << quote_flag(framework, cross_compiling)
         end
       end
 
       flags.join(" ")
     end
 
+    private def quote_flag(flag, cross_compiling)
+      if cross_compiling
+        has_flag?("windows") ? Process.quote_windows(flag) : Process.quote_posix(flag)
+      else
+        Process.quote(flag)
+      end
+    end
+
     # Searches among CRYSTAL_LIBRARY_PATH, the compiler's directory, and PATH
     # for every DLL specified in the used `@[Link]` annotations. Yields the
     # absolute path and `true` if found, the base name and `false` if not found.
diff --git a/src/compiler/crystal/compiler.cr b/src/compiler/crystal/compiler.cr
index f620fe2fb312..aa11ef1dc47e 100644
--- a/src/compiler/crystal/compiler.cr
+++ b/src/compiler/crystal/compiler.cr
@@ -354,7 +354,7 @@ module Crystal
           run_dsymutil(output_filename) unless debug.none?
         {% end %}
 
-        {% if flag?(:windows) %}
+        {% if flag?(:msvc) %}
           copy_dlls(program, output_filename) unless static?
         {% end %}
       end
@@ -424,26 +424,8 @@ module Crystal
 
     private def linker_command(program : Program, object_names, output_filename, output_dir, expand = false)
       if program.has_flag? "msvc"
-        lib_flags = program.lib_flags
-        # Execute and expand `subcommands`.
-        if expand
-          lib_flags = lib_flags.gsub(/`(.*?)`/) do
-            command = $1
-            begin
-              error_io = IO::Memory.new
-              output = Process.run(command, shell: true, output: :pipe, error: error_io) do |process|
-                process.output.gets_to_end
-              end
-              unless $?.success?
-                error_io.rewind
-                error "Error executing subcommand for linker flags: #{command.inspect}: #{error_io}"
-              end
-              output
-            rescue exc
-              error "Error executing subcommand for linker flags: #{command.inspect}: #{exc}"
-            end
-          end
-        end
+        lib_flags = program.lib_flags(@cross_compile)
+        lib_flags = expand_lib_flags(lib_flags) if expand
 
         object_arg = Process.quote_windows(object_names)
         output_arg = Process.quote_windows("/Fe#{output_filename}")
@@ -487,15 +469,63 @@ module Crystal
         {linker, cmd, nil}
       elsif program.has_flag? "wasm32"
         link_flags = @link_flags || ""
-        {"wasm-ld", %(wasm-ld "${@}" -o #{Process.quote_posix(output_filename)} #{link_flags} -lc #{program.lib_flags}), object_names}
+        {"wasm-ld", %(wasm-ld "${@}" -o #{Process.quote_posix(output_filename)} #{link_flags} -lc #{program.lib_flags(@cross_compile)}), object_names}
       elsif program.has_flag? "avr"
         link_flags = @link_flags || ""
         link_flags += " --target=avr-unknown-unknown -mmcu=#{@mcpu} -Wl,--gc-sections"
-        {DEFAULT_LINKER, %(#{DEFAULT_LINKER} "${@}" -o #{Process.quote_posix(output_filename)} #{link_flags} #{program.lib_flags}), object_names}
+        {DEFAULT_LINKER, %(#{DEFAULT_LINKER} "${@}" -o #{Process.quote_posix(output_filename)} #{link_flags} #{program.lib_flags(@cross_compile)}), object_names}
+      elsif program.has_flag?("win32") && program.has_flag?("gnu")
+        link_flags = @link_flags || ""
+        lib_flags = program.lib_flags(@cross_compile)
+        lib_flags = expand_lib_flags(lib_flags) if expand
+        cmd = %(#{DEFAULT_LINKER} #{Process.quote_windows(object_names)} -o #{Process.quote_windows(output_filename)} #{link_flags} #{lib_flags})
+
+        if cmd.size > 32000
+          # The command line would be too big, pass the args through a file instead.
+          # GCC response file does not interpret those args as shell-escaped
+          # arguments, we must rebuild the whole command line
+          args_filename = "#{output_dir}/linker_args.txt"
+          File.open(args_filename, "w") do |f|
+            object_names.each do |object_name|
+              f << object_name.gsub(GCC_RESPONSE_FILE_TR) << ' '
+            end
+            f << "-o " << output_filename.gsub(GCC_RESPONSE_FILE_TR) << ' '
+            f << link_flags << ' ' << lib_flags
+          end
+          cmd = "#{DEFAULT_LINKER} #{Process.quote_windows("@" + args_filename)}"
+        end
+
+        {DEFAULT_LINKER, cmd, nil}
       else
         link_flags = @link_flags || ""
         link_flags += " -rdynamic"
-        {DEFAULT_LINKER, %(#{DEFAULT_LINKER} "${@}" -o #{Process.quote_posix(output_filename)} #{link_flags} #{program.lib_flags}), object_names}
+        {DEFAULT_LINKER, %(#{DEFAULT_LINKER} "${@}" -o #{Process.quote_posix(output_filename)} #{link_flags} #{program.lib_flags(@cross_compile)}), object_names}
+      end
+    end
+
+    private GCC_RESPONSE_FILE_TR = {
+      " ":  %q(\ ),
+      "'":  %q(\'),
+      "\"": %q(\"),
+      "\\": "\\\\",
+    }
+
+    private def expand_lib_flags(lib_flags)
+      lib_flags.gsub(/`(.*?)`/) do
+        command = $1
+        begin
+          error_io = IO::Memory.new
+          output = Process.run(command, shell: true, output: :pipe, error: error_io) do |process|
+            process.output.gets_to_end
+          end
+          unless $?.success?
+            error_io.rewind
+            error "Error executing subcommand for linker flags: #{command.inspect}: #{error_io}"
+          end
+          output.chomp
+        rescue exc
+          error "Error executing subcommand for linker flags: #{command.inspect}: #{exc}"
+        end
       end
     end
 
diff --git a/src/crystal/system/win32/wmain.cr b/src/crystal/system/win32/wmain.cr
index 71383c66a88a..3dd64f9c1b92 100644
--- a/src/crystal/system/win32/wmain.cr
+++ b/src/crystal/system/win32/wmain.cr
@@ -4,7 +4,12 @@ require "c/stdlib"
 
 {% begin %}
   # we have both `main` and `wmain`, so we must choose an unambiguous entry point
-  @[Link({{ flag?(:static) ? "libcmt" : "msvcrt" }}, ldflags: "/ENTRY:wmainCRTStartup")]
+  @[Link({{ flag?(:static) ? "libcmt" : "msvcrt" }})]
+  {% if flag?(:msvc) %}
+    @[Link(ldflags: "/ENTRY:wmainCRTStartup")]
+  {% elsif flag?(:gnu) %}
+    @[Link(ldflags: "-municode")]
+  {% end %}
 {% end %}
 lib LibCrystalMain
 end
diff --git a/src/lib_c/x86_64-windows-msvc/c/stdio.cr b/src/lib_c/x86_64-windows-msvc/c/stdio.cr
index f23bba8503f6..ddfa97235d87 100644
--- a/src/lib_c/x86_64-windows-msvc/c/stdio.cr
+++ b/src/lib_c/x86_64-windows-msvc/c/stdio.cr
@@ -1,6 +1,8 @@
 require "./stddef"
 
-@[Link("legacy_stdio_definitions")]
+{% if flag?(:msvc) %}
+  @[Link("legacy_stdio_definitions")]
+{% end %}
 lib LibC
   # unused
   fun printf(format : Char*, ...) : Int