--- a/dom/base/test/mochitest.ini
+++ b/dom/base/test/mochitest.ini
@@ -290,17 +290,17 @@ skip-if = toolkit == 'android'
 [test_bug311681.xml]
 [test_bug313646.html]
 [test_bug320799.html]
 [test_bug322317.html]
 [test_bug326337.html]
 [test_bug330925.xhtml]
 [test_bug331959.html]
 [test_bug333064.html]
-skip-if = toolkit == 'android' || headless # Headless: Bug 1405868
+skip-if = toolkit == 'android'
 [test_bug333198.html]
 [test_bug333673.html]
 [test_bug337631.html]
 [test_bug338541.xhtml]
 [test_bug338583.html]
 skip-if = toolkit == 'android'
 [test_bug338679.html]
 [test_bug339494.html]

--- a/dom/events/test/mochitest.ini
+++ b/dom/events/test/mochitest.ini
@@ -170,17 +170,16 @@ skip-if = toolkit == 'android' #CRASH_DU
 [test_legacy_event.html]
 [test_messageEvent.html]
 [test_messageEvent_init.html]
 [test_moz_mouse_pixel_scroll_event.html]
 [test_offsetxy.html]
 [test_onerror_handler_args.html]
 [test_passive_listeners.html]
 [test_paste_image.html]
-skip-if = headless # Bug 1405869
 [test_wheel_default_action.html]
 [test_bug687787.html]
 [test_bug1305458.html]
 [test_bug1298970.html]
 [test_bug1304044.html]
 [test_bug1332699.html]
 [test_bug1339758.html]
 [test_bug1369072.html]

--- a/toolkit/components/extensions/test/mochitest/mochitest-common.ini
+++ b/toolkit/components/extensions/test/mochitest/mochitest-common.ini
@@ -56,17 +56,17 @@ support-files =
   return_headers.sjs
   slow_response.sjs
   webrequest_worker.js
   !/toolkit/components/passwordmgr/test/authenticate.sjs
   !/dom/tests/mochitest/geolocation/network_geolocation.sjs
 
 [test_ext_clipboard.html]
 [test_ext_clipboard_image.html]
-skip-if = headless # disabled test case with_permission_allow_copy, see inline comment. Headless: Bug 1405872
+# skip-if = # disabled test case with_permission_allow_copy, see inline comment.
 [test_ext_inIncognitoContext_window.html]
 skip-if = os == 'android' # Android does not support multiple windows.
 [test_ext_geturl.html]
 [test_ext_background_canvas.html]
 [test_ext_content_security_policy.html]
 [test_ext_contentscript_api_injection.html]
 [test_ext_contentscript_async_loading.html]
 skip-if = os == 'android' && debug # The generated script takes too long to load on Android debug

--- a/widget/headless/HeadlessClipboard.cpp
+++ b/widget/headless/HeadlessClipboard.cpp
@@ -1,111 +1,241 @@
 /* This Source Code Form is subject to the terms of the Mozilla Public
  * License, v. 2.0. If a copy of the MPL was not distributed with this
  * file, You can obtain one at http://mozilla.org/MPL/2.0/. */
 
 #include "HeadlessClipboard.h"
 
 #include "nsISupportsPrimitives.h"
 #include "nsComponentManagerUtils.h"
-#include "nsCOMPtr.h"
+#include "nsString.h"
+#include "mozilla/RefPtr.h"
+#include "nsArrayUtils.h"
+#include "imgIContainer.h"
+#include "gfxUtils.h"
+#include "nsIInputStream.h"
+
+using mozilla::gfx::SourceSurface;
+using mozilla::gfx::DataSourceSurface;
 
 namespace mozilla {
 namespace widget {
 
 NS_IMPL_ISUPPORTS(HeadlessClipboard, nsIClipboard)
 
 HeadlessClipboard::HeadlessClipboard()
-  : mClipboard(MakeUnique<HeadlessClipboardData>())
 {
 }
 
 NS_IMETHODIMP
 HeadlessClipboard::SetData(nsITransferable *aTransferable,
                      nsIClipboardOwner *anOwner,
                      int32_t aWhichClipboard)
 {
   if (aWhichClipboard != kGlobalClipboard) {
     return NS_ERROR_NOT_IMPLEMENTED;
   }
 
-  // Clear out the clipboard in order to set the new data.
-  EmptyClipboard(aWhichClipboard);
-
-  // Only support plain text for now.
-  nsCOMPtr<nsISupports> clip;
-  uint32_t len;
-  nsresult rv = aTransferable->GetTransferData(kUnicodeMime,
-                                               getter_AddRefs(clip),
-                                               &len);
-  if (NS_FAILED(rv)) {
-    return rv;
-  }
-  nsCOMPtr<nsISupportsString> wideString = do_QueryInterface(clip);
-  if (!wideString) {
-    return NS_ERROR_NOT_IMPLEMENTED;
-  }
-  nsAutoString utf16string;
-  wideString->GetData(utf16string);
-  mClipboard->SetText(utf16string);
+  mTransferable = aTransferable;
 
   return NS_OK;
 }
 
+// Tries to unwrap aItem and convert it to the requested aOutputFlavor mime
+// type and then set the transfer data on the transferable. Currently, only
+// images are supported.
+bool
+TrySetTransferData(nsISupports* aItem, const char *aOutputFlavor,
+                   nsITransferable *aTransferable)
+{
+  nsCOMPtr<nsISupportsInterfacePointer> ptrPrimitive(do_QueryInterface(aItem));
+  if (!ptrPrimitive) {
+    return false;
+  }
+
+  nsCOMPtr<nsISupports> primitiveData;
+  ptrPrimitive->GetData(getter_AddRefs(primitiveData));
+  nsCOMPtr<imgIContainer> image(do_QueryInterface(primitiveData));
+  if (!image) {
+    return false;
+  }
+
+  RefPtr<SourceSurface> surface =
+    image->GetFrame(imgIContainer::FRAME_CURRENT,
+                    imgIContainer::FLAG_SYNC_DECODE);
+  if (!surface) {
+    return false;
+  }
+  RefPtr<DataSourceSurface> dataSurface = surface->GetDataSurface();
+  nsCOMPtr<nsIInputStream> imgStream;
+  gfxUtils::GetInputStream(dataSurface,
+                           true,
+                           aOutputFlavor,
+                           EmptyString().get(),
+                           getter_AddRefs(imgStream));
+  nsresult rv = aTransferable->SetTransferData(aOutputFlavor,
+                                               imgStream,
+                                               sizeof(nsIInputStream*));
+  return NS_SUCCEEDED(rv);
+}
+
+bool
+HeadlessClipboard::GetSourceFlavor(const char* aRequestedFlavor,
+                                   nsACString &result) {
+  if (!mTransferable) {
+    result.Assign(EmptyCString());
+    return false;
+  }
+  nsCOMPtr<nsIArray> supportedFlavors;
+  nsresult rv =
+    mTransferable->FlavorsTransferableCanExport(getter_AddRefs(supportedFlavors));
+  NS_ENSURE_SUCCESS(rv, false);
+  uint32_t supportedCount;
+  supportedFlavors->GetLength(&supportedCount);
+
+  // First try to see if the requested flavor is supported by default.
+  for (uint32_t i = 0; i < supportedCount; i++) {
+    nsCOMPtr<nsISupportsCString> supportedFlavor =
+      do_QueryElementAt(supportedFlavors, i);
+    if (!supportedFlavor) {
+      continue;
+    }
+    nsAutoCString supportedflavorStr;
+    supportedFlavor->GetData(supportedflavorStr);
+    if (supportedflavorStr.Equals(aRequestedFlavor)) {
+      result.Assign(supportedflavorStr);
+      return true;
+    }
+  }
+
+  // Now try the image formats that are convertible.
+  if (strcmp(aRequestedFlavor, kPNGImageMime) != 0 &&
+      strcmp(aRequestedFlavor, kJPGImageMime) != 0 &&
+      strcmp(aRequestedFlavor, kJPEGImageMime) != 0) {
+    result.Assign(EmptyCString());
+    return false;
+  }
+
+  for (uint32_t i = 0; i < supportedCount; i++) {
+    nsCOMPtr<nsISupportsCString> supportedFlavor =
+      do_QueryElementAt(supportedFlavors, i);
+    if (!supportedFlavor) {
+      continue;
+    }
+    nsAutoCString supportedflavorStr;
+    supportedFlavor->GetData(supportedflavorStr);
+    if (supportedflavorStr.EqualsLiteral(kNativeImageMime) ||
+        supportedflavorStr.EqualsLiteral(kPNGImageMime) ||
+        supportedflavorStr.EqualsLiteral(kJPGImageMime) ||
+        supportedflavorStr.EqualsLiteral(kJPEGImageMime)) {
+      result.Assign(supportedflavorStr);
+      return true;
+    }
+  }
+  result.Assign(EmptyCString());
+  return false;
+}
+
 NS_IMETHODIMP
 HeadlessClipboard::GetData(nsITransferable *aTransferable,
-                     int32_t aWhichClipboard)
+                           int32_t aWhichClipboard)
 {
   if (aWhichClipboard != kGlobalClipboard) {
     return NS_ERROR_NOT_IMPLEMENTED;
   }
 
-  nsresult rv;
-  nsCOMPtr<nsISupportsString> dataWrapper =
-    do_CreateInstance(NS_SUPPORTS_STRING_CONTRACTID, &rv);
-  rv = dataWrapper->SetData(mClipboard->GetText());
-  if (NS_WARN_IF(NS_FAILED(rv))) {
-    return rv;
+  nsCOMPtr<nsIArray> requestedFlavors;
+  nsresult rv =
+    aTransferable->FlavorsTransferableCanImport(getter_AddRefs(requestedFlavors));
+  NS_ENSURE_SUCCESS(rv, rv);
+
+  uint32_t requestedCount;
+  requestedFlavors->GetLength(&requestedCount);
+  // See if the stored transferable supports any of the requested flavors.
+  for (uint32_t i = 0; i < requestedCount; i++) {
+    nsCOMPtr<nsISupportsCString> requestedFlavor =
+      do_QueryElementAt(requestedFlavors, i);
+    if (!requestedFlavor) {
+      continue;
+    }
+    nsAutoCString requestedFlavorStr;
+    rv = requestedFlavor->GetData(requestedFlavorStr);
+    NS_ENSURE_SUCCESS(rv, rv);
+
+    nsAutoCString sourceFlavorStr;
+    if (!GetSourceFlavor(requestedFlavorStr.get(), sourceFlavorStr)) {
+      continue;
+    }
+
+    nsCOMPtr<nsISupports> item;
+    uint32_t len;
+
+    // First, check if the saved transferable supports the requested flavor with
+    // no conversion.
+    if (requestedFlavorStr == sourceFlavorStr) {
+      rv = mTransferable->GetTransferData(requestedFlavorStr.get(),
+                                          getter_AddRefs(item), &len);
+      if (NS_SUCCEEDED(rv)) {
+        aTransferable->SetTransferData(requestedFlavorStr.get(), item, len);
+        return NS_OK;
+      }
+
+      // Under some cases GetTransferData will return a failure, but the item
+      // will still have data that can be unwrapped and converted to an image.
+      if (NS_FAILED(rv) && item &&
+          TrySetTransferData(item, requestedFlavorStr.get(), aTransferable)) {
+        return NS_OK;
+      }
+    } else {
+      // Try to convert the stored transferable to the requested flavor.
+      mTransferable->GetTransferData(sourceFlavorStr.get(),
+                                     getter_AddRefs(item), &len);
+      if (TrySetTransferData(item, requestedFlavorStr.get(), aTransferable)) {
+        return NS_OK;
+      }
+    }
   }
-  nsCOMPtr<nsISupports> genericDataWrapper = do_QueryInterface(dataWrapper);
-  uint32_t len = mClipboard->GetText().Length() * sizeof(char16_t);
-  rv = aTransferable->SetTransferData(kUnicodeMime, genericDataWrapper, len);
-  if (NS_WARN_IF(NS_FAILED(rv))) {
-    return rv;
-  }
+
   return NS_OK;
 }
 
 NS_IMETHODIMP
 HeadlessClipboard::EmptyClipboard(int32_t aWhichClipboard)
 {
   if (aWhichClipboard != kGlobalClipboard) {
     return NS_ERROR_NOT_IMPLEMENTED;
   }
-  mClipboard->Clear();
+  mTransferable = nullptr;
   return NS_OK;
 }
 
 NS_IMETHODIMP
 HeadlessClipboard::HasDataMatchingFlavors(const char **aFlavorList,
-                                    uint32_t aLength, int32_t aWhichClipboard,
-                                    bool *aHasType)
+                                          uint32_t aLength,
+                                          int32_t aWhichClipboard,
+                                          bool *aHasType)
 {
   *aHasType = false;
   if (aWhichClipboard != kGlobalClipboard) {
     return NS_ERROR_NOT_IMPLEMENTED;
   }
+  if (!mTransferable) {
+    return NS_OK;
+  }
+
   // Retrieve the union of all aHasType in aFlavorList
   for (uint32_t i = 0; i < aLength; ++i) {
     const char *flavor = aFlavorList[i];
     if (!flavor) {
       continue;
     }
-    if (!strcmp(flavor, kUnicodeMime) && mClipboard->HasText()) {
+    nsAutoCString result;
+    if (GetSourceFlavor(flavor, result)) {
       *aHasType = true;
+      return NS_OK;
     }
   }
   return NS_OK;
 }
 
 NS_IMETHODIMP
 HeadlessClipboard::SupportsSelectionClipboard(bool *aIsSupported)
 {

--- a/widget/headless/HeadlessClipboard.h
+++ b/widget/headless/HeadlessClipboard.h
@@ -3,33 +3,37 @@
  * License, v. 2.0. If a copy of the MPL was not distributed with this
  * file, You can obtain one at http://mozilla.org/MPL/2.0/. */
 
 
 #ifndef mozilla_widget_HeadlessClipboard_h
 #define mozilla_widget_HeadlessClipboard_h
 
 #include "nsIClipboard.h"
-#include "mozilla/UniquePtr.h"
-#include "HeadlessClipboardData.h"
+#include "nsCOMPtr.h"
 
 namespace mozilla {
 namespace widget {
 
 class HeadlessClipboard final : public nsIClipboard
 {
 public:
   NS_DECL_ISUPPORTS
   NS_DECL_NSICLIPBOARD
 
   HeadlessClipboard();
 
 protected:
   ~HeadlessClipboard() {}
 
 private:
-  UniquePtr<HeadlessClipboardData> mClipboard;
+
+  nsCOMPtr<nsITransferable> mTransferable;
+  // Checks if the stored transferable supports the requested flavor either
+  // by default or with conversion. On success the underlying flavor that can
+  // be used is stored in aSourceFlavor.
+  bool GetSourceFlavor(const char* aRequestedFlavor, nsACString &aSourceFlavor);
 };
 
 } // namespace widget
 } // namespace mozilla
 
 #endif

deleted file mode 100644
--- a/widget/headless/HeadlessClipboardData.cpp
+++ /dev/null
@@ -1,35 +0,0 @@
-/* This Source Code Form is subject to the terms of the Mozilla Public
- * License, v. 2.0. If a copy of the MPL was not distributed with this
- * file, You can obtain one at http://mozilla.org/MPL/2.0/. */
-
-#include "HeadlessClipboardData.h"
-
-namespace mozilla {
-namespace widget {
-
-void
-HeadlessClipboardData::SetText(const nsAString &aText)
-{
-  mPlain = aText;
-}
-
-bool
-HeadlessClipboardData::HasText() const
-{
-  return !mPlain.IsEmpty();
-}
-
-const nsAString&
-HeadlessClipboardData::GetText() const
-{
-  return mPlain;
-}
-
-void
-HeadlessClipboardData::Clear()
-{
-  mPlain.Truncate(0);
-}
-
-} // namespace widget
-} // namespace mozilla

deleted file mode 100644
--- a/widget/headless/HeadlessClipboardData.h
+++ /dev/null
@@ -1,35 +0,0 @@
-/* This Source Code Form is subject to the terms of the Mozilla Public
- * License, v. 2.0. If a copy of the MPL was not distributed with this
- * file, You can obtain one at http://mozilla.org/MPL/2.0/. */
-
-#ifndef mozilla_widget_HeadlessClipboardData_h
-#define mozilla_widget_HeadlessClipboardData_h
-
-#include "mozilla/RefPtr.h"
-#include "nsString.h"
-
-namespace mozilla {
-namespace widget {
-
-class HeadlessClipboardData final
-{
-public:
-  explicit HeadlessClipboardData() = default;
-  ~HeadlessClipboardData() = default;
-
-  // For text/plain
-  void SetText(const nsAString &aText);
-  bool HasText() const;
-  const nsAString& GetText() const;
-
-  // For other APIs
-  void Clear();
-
-private:
-  nsAutoString mPlain;
-};
-
-} // namespace widget
-} // namespace mozilla
-
-#endif // mozilla_widget_HeadlessClipboardData_h

--- a/widget/headless/moz.build
+++ b/widget/headless/moz.build
@@ -20,17 +20,16 @@ if widget_dir in ('gtk3', 'gtk2'):
     widget_dir = 'gtk'
 
 LOCAL_INCLUDES += [
     '/widget/%s' % widget_dir,
 ]
 
 UNIFIED_SOURCES += [
     'HeadlessClipboard.cpp',
-    'HeadlessClipboardData.cpp',
     'HeadlessCompositorWidget.cpp',
     'HeadlessScreenHelper.cpp',
     'HeadlessSound.cpp',
     'HeadlessWidget.cpp',
 ]
 
 if widget_dir == 'gtk':
     UNIFIED_SOURCES += [