diff --git a/src/catch2/internal/catch_console_colour.cpp b/src/catch2/internal/catch_console_colour.cpp
index 142de9e65e..878407bfcc 100644
--- a/src/catch2/internal/catch_console_colour.cpp
+++ b/src/catch2/internal/catch_console_colour.cpp
@@ -97,7 +97,6 @@ namespace Catch {
 
 } // namespace Catch
 
-
 #if defined ( CATCH_CONFIG_COLOUR_WIN32 ) /////////////////////////////////////////
 
 namespace Catch {
@@ -115,10 +114,13 @@ namespace {
         }
 
         static bool useImplementationForStream(IStream const& stream) {
-            // Win32 text colour APIs can only be used on console streams
-            // We cannot check that the output hasn't been redirected,
-            // so we just check that the original stream is console stream.
-            return stream.isConsole();
+            OSVERSIONINFOA versionInfo;
+            // Use as fallback for Windows versions <10.0 only.
+            // Newer Windows versions have full support for ANSI color codes.
+            if ( GetVersionExA( &versionInfo ) && versionInfo.dwMajorVersion < 10 ) {
+                return stream.isConsole();
+            }
+            return false;
         }
 
     private:
@@ -160,48 +162,23 @@ namespace {
 
 #endif // Windows/ ANSI/ None
 
-
-#if defined( CATCH_PLATFORM_LINUX ) || defined( CATCH_PLATFORM_MAC ) || defined( __GLIBC__ )
-#    define CATCH_INTERNAL_HAS_ISATTY
-#    include <unistd.h>
-#endif
-
 namespace Catch {
 namespace {
 
     class ANSIColourImpl final : public ColourImpl {
     public:
-        ANSIColourImpl( IStream* stream ): ColourImpl( stream ) {}
+        ANSIColourImpl( IStream* stream ): ColourImpl( stream ) {
+        }
 
         static bool useImplementationForStream(IStream const& stream) {
-            // This is kinda messy due to trying to support a bunch of
-            // different platforms at once.
-            // The basic idea is that if we are asked to do autodetection (as
-            // opposed to being told to use posixy colours outright), then we
-            // only want to use the colours if we are writing to console.
-            // However, console might be redirected, so we make an attempt at
-            // checking for that on platforms where we know how to do that.
-            bool useColour = stream.isConsole();
-#if defined( CATCH_INTERNAL_HAS_ISATTY ) && \
-    !( defined( __DJGPP__ ) && defined( __STRICT_ANSI__ ) )
-            ErrnoGuard _; // for isatty
-            useColour = useColour && isatty( STDOUT_FILENO );
-#    endif
-#    if defined( CATCH_PLATFORM_MAC ) || defined( CATCH_PLATFORM_IPHONE )
-            useColour = useColour && !isDebuggerActive();
-#    endif
-
-            return useColour;
+            return stream.isConsole();
         }
 
     private:
         void use( Colour::Code _colourCode ) const override {
             auto setColour = [&out =
                                   m_stream->stream()]( char const* escapeCode ) {
-                // The escape sequence must be flushed to console, otherwise
-                // if stdin and stderr are intermixed, we'd get accidentally
-                // coloured output.
-                out << '\033' << escapeCode << std::flush;
+                out << '\033' << escapeCode;
             };
             switch( _colourCode ) {
                 case Colour::None:
diff --git a/src/catch2/internal/catch_istream.cpp b/src/catch2/internal/catch_istream.cpp
index 717da0e78c..e2eeb8b738 100644
--- a/src/catch2/internal/catch_istream.cpp
+++ b/src/catch2/internal/catch_istream.cpp
@@ -6,15 +6,25 @@
 
 // SPDX-License-Identifier: BSL-1.0
 
-#include <catch2/internal/catch_istream.hpp>
-#include <catch2/internal/catch_enforce.hpp>
 #include <catch2/internal/catch_debug_console.hpp>
-#include <catch2/internal/catch_unique_ptr.hpp>
+#include <catch2/internal/catch_enforce.hpp>
+#include <catch2/internal/catch_errno_guard.hpp>
+#include <catch2/internal/catch_istream.hpp>
 #include <catch2/internal/catch_stdstreams.hpp>
+#include <catch2/internal/catch_unique_ptr.hpp>
+#include <catch2/internal/catch_windows_h_proxy.hpp>
 
 #include <cstdio>
 #include <fstream>
 
+#if defined( CATCH_PLATFORM_LINUX ) || defined( CATCH_PLATFORM_MAC ) || \
+    defined( __GLIBC__ )
+#    define CATCH_INTERNAL_HAS_ISATTY
+#    include <unistd.h>
+#elif defined( CATCH_PLATFORM_WINDOWS )
+#    include <io.h>
+#endif
+
 namespace Catch {
 
     Catch::IStream::~IStream() = default;
@@ -86,29 +96,78 @@ namespace Detail {
 
         ///////////////////////////////////////////////////////////////////////////
 
+#if defined( CATCH_PLATFORM_WINDOWS )
+        bool enableVirtualTerminalSupport( DWORD stdHandle ) {
+            HANDLE outputHandle = GetStdHandle( stdHandle );
+            DWORD mode = 0;
+            const DWORD requiredMode = ENABLE_PROCESSED_OUTPUT |
+                                ENABLE_VIRTUAL_TERMINAL_PROCESSING;
+            if ( GetConsoleMode( outputHandle, &mode ) &&
+                    ( mode & requiredMode ) == requiredMode ) {
+                // VT100 style sequence processing has to be enabled by
+                // explicit opt-in.
+                const DWORD newMode = mode | requiredMode;
+                if( SetConsoleMode( outputHandle, newMode ) )
+                {
+                    return true;
+                }
+                // Restore fail-safe state.
+                SetConsoleMode( outputHandle, mode );
+            }
+            return false;
+        }
+#endif
+
         class CoutStream final : public IStream {
             std::ostream m_os;
+            bool m_isatty;
         public:
             // Store the streambuf from cout up-front because
             // cout may get redirected when running tests
-            CoutStream() : m_os( Catch::cout().rdbuf() ) {}
+            CoutStream() : m_os( Catch::cout().rdbuf() ) {
+                m_isatty = true;
+#if defined( CATCH_INTERNAL_HAS_ISATTY ) && \
+    !( defined( __DJGPP__ ) && defined( __STRICT_ANSI__ ) )
+                ErrnoGuard _; // for isatty
+                m_isatty = m_isatty && isatty( STDOUT_FILENO );
+#elif defined( CATCH_PLATFORM_WINDOWS )
+                m_isatty = m_isatty && _isatty( _fileno( stdout ) );
+                m_isatty = m_isatty && enableVirtualTerminalSupport( STD_OUTPUT_HANDLE );
+#endif
+#if defined( CATCH_PLATFORM_MAC ) || defined( CATCH_PLATFORM_IPHONE )
+                m_isatty = m_isatty && !isDebuggerActive();
+#endif
+            }
 
         public: // IStream
             std::ostream& stream() override { return m_os; }
-            bool isConsole() const override { return true; }
+            bool isConsole() const override { return m_isatty; }
         };
 
         class CerrStream : public IStream {
             std::ostream m_os;
-
+            bool m_isatty;
         public:
             // Store the streambuf from cerr up-front because
             // cout may get redirected when running tests
-            CerrStream(): m_os( Catch::cerr().rdbuf() ) {}
+            CerrStream(): m_os( Catch::cerr().rdbuf() ) {
+                m_isatty = true;
+#if defined( CATCH_INTERNAL_HAS_ISATTY ) && \
+    !( defined( __DJGPP__ ) && defined( __STRICT_ANSI__ ) )
+                ErrnoGuard _; // for isatty
+                m_isatty = m_isatty && isatty( STDERR_FILENO );
+#elif defined( CATCH_PLATFORM_WINDOWS )
+                m_isatty = m_isatty && _isatty( _fileno( stderr ) );
+                m_isatty = m_isatty && enableVirtualTerminalSupport( STD_ERROR_HANDLE );
+#endif
+#if defined( CATCH_PLATFORM_MAC ) || defined( CATCH_PLATFORM_IPHONE )
+                m_isatty = m_isatty && !isDebuggerActive();
+#endif
+            }
 
         public: // IStream
             std::ostream& stream() override { return m_os; }
-            bool isConsole() const override { return true; }
+            bool isConsole() const override { return m_isatty; }
         };
 
         ///////////////////////////////////////////////////////////////////////////