diff --git a/.github/workflows/win.yml b/.github/workflows/win.yml
index 9cd1eae3e809..0890978d334c 100644
--- a/.github/workflows/win.yml
+++ b/.github/workflows/win.yml
@@ -278,7 +278,6 @@ jobs:
           echo "CRYSTAL_LIBRARY_PATH=$(pwd)\libs" >> ${env:GITHUB_ENV}
           echo 'CRYSTAL_CONFIG_PATH=$ORIGIN\src' >> ${env:GITHUB_ENV}
           echo 'CRYSTAL_CONFIG_LIBRARY_PATH=$ORIGIN\lib' >> ${env:GITHUB_ENV}
-          echo "TERM=dumb" >> ${env:GITHUB_ENV}
           echo "LLVM_CONFIG=$(pwd)\llvm\bin\llvm-config.exe" >> ${env:GITHUB_ENV}
           echo "CRYSTAL_CONFIG_BUILD_COMMIT=$(git rev-parse --short=9 HEAD)" >> ${env:GITHUB_ENV}
           echo "SOURCE_DATE_EPOCH=$(Get-Date -Millisecond 0 -UFormat %s)" >> ${env:GITHUB_ENV}
diff --git a/src/crystal/system/win32/file_descriptor.cr b/src/crystal/system/win32/file_descriptor.cr
index cc9ee508c2be..d9013bb90bc2 100644
--- a/src/crystal/system/win32/file_descriptor.cr
+++ b/src/crystal/system/win32/file_descriptor.cr
@@ -170,8 +170,14 @@ module Crystal::System::FileDescriptor
     console_handle = false
     handle = LibC._get_osfhandle(fd)
     if handle != -1
-      if LibC.GetConsoleMode(LibC::HANDLE.new(handle), out _) != 0
+      handle = LibC::HANDLE.new(handle)
+      if LibC.GetConsoleMode(handle, out old_mode) != 0
         console_handle = true
+        if fd == 1 || fd == 2 # STDOUT or STDERR
+          if LibC.SetConsoleMode(handle, old_mode | LibC::ENABLE_VIRTUAL_TERMINAL_PROCESSING) != 0
+            at_exit { LibC.SetConsoleMode(handle, old_mode) }
+          end
+        end
       end
     end
 
diff --git a/src/lib_c/x86_64-windows-msvc/c/consoleapi.cr b/src/lib_c/x86_64-windows-msvc/c/consoleapi.cr
index 8eb8467eb3c5..90693df681ce 100644
--- a/src/lib_c/x86_64-windows-msvc/c/consoleapi.cr
+++ b/src/lib_c/x86_64-windows-msvc/c/consoleapi.cr
@@ -1,7 +1,10 @@
 require "c/winnt"
 
 lib LibC
+  ENABLE_VIRTUAL_TERMINAL_PROCESSING = 0x0004
+
   fun GetConsoleMode(hConsoleHandle : HANDLE, lpMode : DWORD*) : BOOL
+  fun SetConsoleMode(hConsoleHandle : HANDLE, dwMode : DWORD) : BOOL
 
   fun GetConsoleCP : DWORD
   fun GetConsoleOutputCP : DWORD