diff --git a/spec/std/process_spec.cr b/spec/std/process_spec.cr
index 57f90121c26b..08ba14058905 100644
--- a/spec/std/process_spec.cr
+++ b/spec/std/process_spec.cr
@@ -479,6 +479,27 @@ pending_interpreted describe: Process do
   {% end %}
 
   describe ".exec" do
+    it "redirects STDIN and STDOUT to files", tags: %w[slow] do
+      with_tempfile("crystal-exec-stdin", "crystal-exec-stdout") do |stdin_path, stdout_path|
+        File.write(stdin_path, "foobar")
+
+        status, _, _ = compile_and_run_source <<-CRYSTAL
+          command = #{stdin_to_stdout_command[0].inspect}
+          args = #{stdin_to_stdout_command[1].to_a} of String
+          stdin_path = #{stdin_path.inspect}
+          stdout_path = #{stdout_path.inspect}
+          File.open(stdin_path) do |input|
+            File.open(stdout_path, "w") do |output|
+              Process.exec(command, args, input: input, output: output)
+            end
+          end
+          CRYSTAL
+
+        status.success?.should be_true
+        File.read(stdout_path).chomp.should eq("foobar")
+      end
+    end
+
     it "gets error from exec" do
       expect_raises(File::NotFoundError, "Error executing process: 'foobarbaz'") do
         Process.exec("foobarbaz")
diff --git a/src/crystal/system/win32/process.cr b/src/crystal/system/win32/process.cr
index 2c6d81720636..7031654d2299 100644
--- a/src/crystal/system/win32/process.cr
+++ b/src/crystal/system/win32/process.cr
@@ -326,9 +326,9 @@ struct Crystal::System::Process
   end
 
   private def self.try_replace(command_args, env, clear_env, input, output, error, chdir)
-    reopen_io(input, ORIGINAL_STDIN)
-    reopen_io(output, ORIGINAL_STDOUT)
-    reopen_io(error, ORIGINAL_STDERR)
+    old_input_fd = reopen_io(input, ORIGINAL_STDIN)
+    old_output_fd = reopen_io(output, ORIGINAL_STDOUT)
+    old_error_fd = reopen_io(error, ORIGINAL_STDERR)
 
     ENV.clear if clear_env
     env.try &.each do |key, val|
@@ -351,11 +351,18 @@ struct Crystal::System::Process
     argv << Pointer(LibC::WCHAR).null
 
     LibC._wexecvp(command, argv)
+
+    # exec failed; restore the original C runtime file descriptors
+    errno = Errno.value
+    LibC._dup2(old_input_fd, 0)
+    LibC._dup2(old_output_fd, 1)
+    LibC._dup2(old_error_fd, 2)
+    errno
   end
 
   def self.replace(command_args, env, clear_env, input, output, error, chdir) : NoReturn
-    try_replace(command_args, env, clear_env, input, output, error, chdir)
-    raise_exception_from_errno(command_args.is_a?(String) ? command_args : command_args[0])
+    errno = try_replace(command_args, env, clear_env, input, output, error, chdir)
+    raise_exception_from_errno(command_args.is_a?(String) ? command_args : command_args[0], errno)
   end
 
   private def self.raise_exception_from_errno(command, errno = Errno.value)
@@ -367,21 +374,41 @@ struct Crystal::System::Process
     end
   end
 
+  # Replaces the C standard streams' file descriptors, not Win32's, since
+  # `try_replace` uses the C `LibC._wexecvp` and only cares about the former.
+  # Returns a duplicate of the original file descriptor
   private def self.reopen_io(src_io : IO::FileDescriptor, dst_io : IO::FileDescriptor)
-    src_io = to_real_fd(src_io)
+    unless src_io.system_blocking?
+      raise IO::Error.new("Non-blocking streams are not supported in `Process.exec`", target: src_io)
+    end
 
-    dst_io.reopen(src_io)
-    dst_io.blocking = true
-    dst_io.close_on_exec = false
-  end
+    src_fd =
+      case src_io
+      when STDIN  then 0
+      when STDOUT then 1
+      when STDERR then 2
+      else
+        LibC._open_osfhandle(src_io.windows_handle, 0)
+      end
 
-  private def self.to_real_fd(fd : IO::FileDescriptor)
-    case fd
-    when STDIN  then ORIGINAL_STDIN
-    when STDOUT then ORIGINAL_STDOUT
-    when STDERR then ORIGINAL_STDERR
-    else             fd
+    dst_fd =
+      case dst_io
+      when ORIGINAL_STDIN  then 0
+      when ORIGINAL_STDOUT then 1
+      when ORIGINAL_STDERR then 2
+      else
+        raise "BUG: Invalid destination IO"
+      end
+
+    return src_fd if dst_fd == src_fd
+
+    orig_src_fd = LibC._dup(src_fd)
+
+    if LibC._dup2(src_fd, dst_fd) == -1
+      raise IO::Error.from_errno("Failed to replace C file descriptor", target: dst_io)
     end
+
+    orig_src_fd
   end
 
   def self.chroot(path)
diff --git a/src/lib_c/x86_64-windows-msvc/c/io.cr b/src/lib_c/x86_64-windows-msvc/c/io.cr
index 75da8c18e5b9..ccbaa15f2d1b 100644
--- a/src/lib_c/x86_64-windows-msvc/c/io.cr
+++ b/src/lib_c/x86_64-windows-msvc/c/io.cr
@@ -2,12 +2,13 @@ require "c/stdint"
 
 lib LibC
   fun _wexecvp(cmdname : WCHAR*, argv : WCHAR**) : IntPtrT
+  fun _open_osfhandle(osfhandle : HANDLE, flags : LibC::Int) : LibC::Int
+  fun _dup(fd : Int) : Int
+  fun _dup2(fd1 : Int, fd2 : Int) : Int
 
   # unused
-  fun _open_osfhandle(osfhandle : HANDLE, flags : LibC::Int) : LibC::Int
   fun _get_osfhandle(fd : Int) : IntPtrT
   fun _close(fd : Int) : Int
-  fun _dup2(fd1 : Int, fd2 : Int) : Int
   fun _isatty(fd : Int) : Int
   fun _write(fd : Int, buffer : UInt8*, count : UInt) : Int
   fun _read(fd : Int, buffer : UInt8*, count : UInt) : Int