diff --git a/src/Symfony/Bridge/PhpUnit/DeprecationErrorHandler.php b/src/Symfony/Bridge/PhpUnit/DeprecationErrorHandler.php
index b0f241c862..2b5c734c54 100644
--- a/src/Symfony/Bridge/PhpUnit/DeprecationErrorHandler.php
+++ b/src/Symfony/Bridge/PhpUnit/DeprecationErrorHandler.php
@@ -178,17 +178,38 @@ class DeprecationErrorHandler
         }
     }
 
+    /**
+     * Returns true if STDOUT is defined and supports colorization.
+     *
+     * Reference: Composer\XdebugHandler\Process::supportsColor
+     * https://github.com/composer/xdebug-handler
+     *
+     * @return bool
+     */
     private static function hasColorSupport()
     {
-        if ('\\' === DIRECTORY_SEPARATOR) {
-            return
-                defined('STDOUT') && function_exists('sapi_windows_vt100_support') && sapi_windows_vt100_support(STDOUT)
-                || '10.0.10586' === PHP_WINDOWS_VERSION_MAJOR.'.'.PHP_WINDOWS_VERSION_MINOR.'.'.PHP_WINDOWS_VERSION_BUILD
+        if (!defined('STDOUT')) {
+            return false;
+        }
+
+        if (DIRECTORY_SEPARATOR === '\\') {
+            return (function_exists('sapi_windows_vt100_support')
+                && sapi_windows_vt100_support(STDOUT))
                 || false !== getenv('ANSICON')
                 || 'ON' === getenv('ConEmuANSI')
                 || 'xterm' === getenv('TERM');
         }
 
-        return defined('STDOUT') && function_exists('posix_isatty') && @posix_isatty(STDOUT);
+        if (function_exists('stream_isatty')) {
+            return stream_isatty(STDOUT);
+        }
+
+        if (function_exists('posix_isatty')) {
+            return posix_isatty(STDOUT);
+        }
+
+        $stat = fstat(STDOUT);
+        // Check if formatted mode is S_IFCHR
+        return $stat ? 0020000 === ($stat['mode'] & 0170000) : false;
     }
 }
diff --git a/src/Symfony/Component/Console/Output/StreamOutput.php b/src/Symfony/Component/Console/Output/StreamOutput.php
index 182622a29a..b0897b206f 100644
--- a/src/Symfony/Component/Console/Output/StreamOutput.php
+++ b/src/Symfony/Component/Console/Output/StreamOutput.php
@@ -81,31 +81,34 @@ class StreamOutput extends Output
      *
      * Colorization is disabled if not supported by the stream:
      *
-     *  -  the stream is redirected (eg php file.php >log)
-     *  -  Windows without VT100 support, Ansicon, ConEmu, Mintty
-     *  -  non tty consoles
+     * This is tricky on Windows, because Cygwin, Msys2 etc emulate pseudo
+     * terminals via named pipes, so we can only check the environment.
+     *
+     * Reference: Composer\XdebugHandler\Process::supportsColor
+     * https://github.com/composer/xdebug-handler
      *
      * @return bool true if the stream supports colorization, false otherwise
      */
     protected function hasColorSupport()
     {
-        if (function_exists('stream_isatty') && !@stream_isatty($this->stream)) {
-            return false;
-        }
         if (DIRECTORY_SEPARATOR === '\\') {
-            if (function_exists('sapi_windows_vt100_support')) {
-                $vt100Enabled = @sapi_windows_vt100_support($this->stream);
-            } else {
-                $vt100Enabled = '10.0.10586' === PHP_WINDOWS_VERSION_MAJOR.'.'.PHP_WINDOWS_VERSION_MINOR.'.'.PHP_WINDOWS_VERSION_BUILD;
-            }
-
-            return
-                $vt100Enabled
+            return (function_exists('sapi_windows_vt100_support')
+                && @sapi_windows_vt100_support($this->stream))
                 || false !== getenv('ANSICON')
                 || 'ON' === getenv('ConEmuANSI')
                 || 'xterm' === getenv('TERM');
         }
 
-        return function_exists('posix_isatty') && @posix_isatty($this->stream);
+        if (function_exists('stream_isatty')) {
+            return @stream_isatty($this->stream);
+        }
+
+        if (function_exists('posix_isatty')) {
+            return @posix_isatty($this->stream);
+        }
+
+        $stat = @fstat($this->stream);
+        // Check if formatted mode is S_IFCHR
+        return $stat ? 0020000 === ($stat['mode'] & 0170000) : false;
     }
 }
diff --git a/src/Symfony/Component/VarDumper/Dumper/CliDumper.php b/src/Symfony/Component/VarDumper/Dumper/CliDumper.php
index 689ada77c2..8f3f7c7e99 100644
--- a/src/Symfony/Component/VarDumper/Dumper/CliDumper.php
+++ b/src/Symfony/Component/VarDumper/Dumper/CliDumper.php
@@ -58,7 +58,7 @@ class CliDumper extends AbstractDumper
     {
         parent::__construct($output, $charset);
 
-        if ('\\' === DIRECTORY_SEPARATOR && 'ON' !== @getenv('ConEmuANSI') && 'xterm' !== @getenv('TERM')) {
+        if ('\\' === DIRECTORY_SEPARATOR && !$this->isWindowsTrueColor()) {
             // Use only the base 16 xterm colors when using ANSICON or standard Windows 10 CLI
             $this->setStyles(array(
                 'default' => '31',
@@ -420,7 +420,7 @@ class CliDumper extends AbstractDumper
     protected function supportsColors()
     {
         if ($this->outputStream !== static::$defaultOutput) {
-            return @(is_resource($this->outputStream) && function_exists('posix_isatty') && posix_isatty($this->outputStream));
+            return $this->hasColorSupport($this->outputStream);
         }
         if (null !== static::$defaultColors) {
             return static::$defaultColors;
@@ -448,23 +448,10 @@ class CliDumper extends AbstractDumper
             }
         }
 
-        if ('\\' === DIRECTORY_SEPARATOR) {
-            static::$defaultColors = @(
-                function_exists('sapi_windows_vt100_support') && sapi_windows_vt100_support($this->outputStream)
-                || '10.0.10586' === PHP_WINDOWS_VERSION_MAJOR.'.'.PHP_WINDOWS_VERSION_MINOR.'.'.PHP_WINDOWS_VERSION_BUILD
-                || false !== getenv('ANSICON')
-                || 'ON' === getenv('ConEmuANSI')
-                || 'xterm' === getenv('TERM')
-            );
-        } elseif (function_exists('posix_isatty')) {
-            $h = stream_get_meta_data($this->outputStream) + array('wrapper_type' => null);
-            $h = 'Output' === $h['stream_type'] && 'PHP' === $h['wrapper_type'] ? fopen('php://stdout', 'wb') : $this->outputStream;
-            static::$defaultColors = @posix_isatty($h);
-        } else {
-            static::$defaultColors = false;
-        }
+        $h = stream_get_meta_data($this->outputStream) + array('wrapper_type' => null);
+        $h = 'Output' === $h['stream_type'] && 'PHP' === $h['wrapper_type'] ? fopen('php://stdout', 'wb') : $this->outputStream;
 
-        return static::$defaultColors;
+        return static::$defaultColors = $this->hasColorSupport($h);
     }
 
     /**
@@ -477,4 +464,69 @@ class CliDumper extends AbstractDumper
         }
         parent::dumpLine($depth);
     }
+
+    /**
+     * Returns true if the stream supports colorization.
+     *
+     * Reference: Composer\XdebugHandler\Process::supportsColor
+     * https://github.com/composer/xdebug-handler
+     *
+     * @param mixed $stream A CLI output stream
+     *
+     * @return bool
+     */
+    private function hasColorSupport($stream)
+    {
+        if (!is_resource($stream) || 'stream' !== get_resource_type($stream)) {
+            return false;
+        }
+
+        if (DIRECTORY_SEPARATOR === '\\') {
+            return (function_exists('sapi_windows_vt100_support')
+                && @sapi_windows_vt100_support($stream))
+                || false !== getenv('ANSICON')
+                || 'ON' === getenv('ConEmuANSI')
+                || 'xterm' === getenv('TERM');
+        }
+
+        if (function_exists('stream_isatty')) {
+            return @stream_isatty($stream);
+        }
+
+        if (function_exists('posix_isatty')) {
+            return @posix_isatty($stream);
+        }
+
+        $stat = @fstat($stream);
+        // Check if formatted mode is S_IFCHR
+        return $stat ? 0020000 === ($stat['mode'] & 0170000) : false;
+    }
+
+    /**
+     * Returns true if the Windows terminal supports true color.
+     *
+     * Note that this does not check an output stream, but relies on environment
+     * variables from known implementations, or a PHP and Windows version that
+     * supports true color.
+     *
+     * @return bool
+     */
+    private function isWindowsTrueColor()
+    {
+        $result = strval(getenv('ANSICON_VER')) >= '183'
+            || 'ON' === getenv('ConEmuANSI')
+            || 'xterm' === getenv('TERM');
+
+        if (!$result && PHP_VERSION_ID >= 70200) {
+            $version = sprintf(
+                '%s.%s.%s',
+                PHP_WINDOWS_VERSION_MAJOR,
+                PHP_WINDOWS_VERSION_MINOR,
+                PHP_WINDOWS_VERSION_BUILD
+            );
+            $result = $version >= '10.0.15063';
+        }
+
+        return $result;
+    }
 }