diff --git a/src/calibre/devices/kindle/driver.py b/src/calibre/devices/kindle/driver.py
index 6e8bf8b8fb..935e9a4949 100644
--- a/src/calibre/devices/kindle/driver.py
+++ b/src/calibre/devices/kindle/driver.py
@@ -285,10 +285,10 @@ class KINDLE(USBMS):
 class KINDLE2(KINDLE):
 
     name           = 'Kindle 2/3/4/Touch Device Interface'
-    description    = _('Communicate with the Kindle 2/3 eBook reader.')
+    description    = _('Communicate with the Kindle 2/3/4/Touch eBook reader.')
 
     FORMATS        = KINDLE.FORMATS + ['pdf', 'azw4', 'pobi']
-    DELETE_EXTS    = KINDLE.DELETE_EXTS + ['.mbp1', '.mbs']
+    DELETE_EXTS    = KINDLE.DELETE_EXTS + ['.mbp1', '.mbs', '.sdr']
 
     PRODUCT_ID = [0x0002, 0x0004]
     BCD        = [0x0100]
@@ -347,6 +347,12 @@ class KINDLE2(KINDLE):
                 if h in path_map:
                     book.device_collections = list(sorted(path_map[h]))
 
+    # Detect if the product family needs .apnx files uploaded to sidecar folder
+    def post_open_callback(self):
+        product_id = self.device_being_opened[1]
+        # 4 for for Kindle 4 and 6 for Kindle Fire
+        self.sidecar_apnx = product_id in {0x4, 0x6}
+
     def upload_cover(self, path, filename, metadata, filepath):
         '''
         Hijacking this function to write the apnx file.
@@ -358,6 +364,13 @@ class KINDLE2(KINDLE):
         if os.path.splitext(filepath.lower())[1] not in ('.azw', '.mobi', '.prc'):
             return
 
+        # Create the sidecar folder if necessary
+        if (self.sidecar_apnx):
+            path = os.path.join(os.path.dirname(filepath), filename+".sdr")
+
+            if not os.path.exists(path):
+                os.makedirs(path)
+
         apnx_path = '%s.apnx' % os.path.join(path, filename)
         apnx_builder = APNXBuilder()
         try:
diff --git a/src/calibre/devices/usbms/driver.py b/src/calibre/devices/usbms/driver.py
index ff2b6f3891..70b30e98a6 100644
--- a/src/calibre/devices/usbms/driver.py
+++ b/src/calibre/devices/usbms/driver.py
@@ -10,7 +10,7 @@ driver. It is intended to be subclassed with the relevant parts implemented
 for a particular device.
 '''
 
-import os, re, time, json, uuid, functools
+import os, re, time, json, uuid, functools, shutil
 from itertools import cycle
 
 from calibre.constants import numeric_version
@@ -339,10 +339,13 @@ class USBMS(CLI, Device):
 
                 filepath = os.path.splitext(path)[0]
                 for ext in self.DELETE_EXTS:
-                    if os.path.exists(filepath + ext):
-                        os.unlink(filepath + ext)
-                    if os.path.exists(path + ext):
-                        os.unlink(path + ext)
+                    for x in (filepath, path):
+                        x += ext
+                        if os.path.exists(x):
+                            if os.path.isdir(x):
+                                shutil.rmtree(x, ignore_errors=True)
+                            else:
+                                os.unlink(x)
 
                 if self.SUPPORTS_SUB_DIRS:
                     try: