diff --git a/pkgs/applications/misc/calibre/default.nix b/pkgs/applications/misc/calibre/default.nix
index 327596006091..fe5227e395b4 100644
--- a/pkgs/applications/misc/calibre/default.nix
+++ b/pkgs/applications/misc/calibre/default.nix
@@ -1,29 +1,50 @@
-{ stdenv, fetchurl, python, pyqt5, sip, poppler_utils, pkgconfig, libpng
+{ stdenv, fetchurl, fetchpatch, python, pyqt5, sip, poppler_utils, pkgconfig, libpng
 , imagemagick, libjpeg, fontconfig, podofo, qtbase, qmakeHook, icu, sqlite
 , makeWrapper, unrarSupport ? false, chmlib, pythonPackages, xz, libusb1, libmtp
 , xdg_utils, makeDesktopItem
 }:
 
 stdenv.mkDerivation rec {
-  version = "2.64.0";
+  version = "2.66.0";
   name = "calibre-${version}";
 
   src = fetchurl {
     url = "https://download.calibre-ebook.com/${version}/${name}.tar.xz";
-    sha256 = "0jjbkhd3n7rh5q6cl6yy51hyjbxmgm6xj7i2a1d3h2ggrip1zmr9";
+    sha256 = "1dbv6p9cq9zj51zvhfy2b7aic2zqa44lmfmq7k7fkqcgb6wmanic";
   };
 
   inherit python;
 
   patches = [
-    # Patch from Debian that switches the version update change from
-    # enabled by default to disabled by default.
-    ./no_updates_dialog.patch
+    # Patches from Debian that:
+    # - disable plugin installation (very insecure)
+    # - disables loading of web bug for privacy
+    # - switches the version update from enabled to disabled by default
+    (fetchpatch {
+      name = "disable_plugins.patch";
+      url = "http://bazaar.launchpad.net/~calibre-packagers/calibre/debian/download/head:/disable_plugins.py-20111220183043-dcl08ccfagjxt1dv-1/disable_plugins.py";
+      sha256 = "19spdx52dhbrfn9lm084yl3cfwm6f90imd51k97sf7flmpl569pk";
+    })
+    (fetchpatch {
+      name = "links_privacy.patch";
+      url = "http://bazaar.launchpad.net/~calibre-packagers/calibre/debian/download/head:/linksprivacy.patch-20160417214308-6hvive72pc0r4awc-1/links-privacy.patch";
+      sha256 = "0f6pq2b7q56pxrq2j8yqd7bksc623q2zgq29qcli30f13vga1w60";
+    })
+    (fetchpatch {
+      name = "no_updates_dialog.patch";
+      url = "http://bazaar.launchpad.net/~calibre-packagers/calibre/debian/download/head:/no_updates_dialog.pa-20081231120426-rzzufl0zo66t3mtc-16/no_updates_dialog.patch";
+      sha256 = "16xwa2fa47jvs954fjrwr8rhh89aljgi1d1wrfxa40sknlmfwxif";
+    })
+    # the unrar patch is not from debian
   ] ++ stdenv.lib.optional (!unrarSupport) ./dont_build_unrar_plugin.patch;
 
   prePatch = ''
     sed -i "/pyqt_sip_dir/ s:=.*:= '${pyqt5}/share/sip/PyQt5':"  \
       setup/build_environment.py
+
+    # Remove unneeded files and libs
+    rm -rf resources/calibre-portable.* \
+           src/{chardet,cherrypy,html5lib,odf,routes}
   '';
 
   dontUseQmakeConfigure = true;
@@ -34,14 +55,14 @@ stdenv.mkDerivation rec {
 
   nativeBuildInputs = [ makeWrapper pkgconfig qmakeHook ];
 
-  buildInputs =
-    [ python pyqt5 sip poppler_utils libpng imagemagick libjpeg
-      fontconfig podofo qtbase chmlib icu sqlite libusb1 libmtp xdg_utils
-      pythonPackages.mechanize pythonPackages.lxml pythonPackages.dateutil
-      pythonPackages.cssutils pythonPackages.beautifulsoup pythonPackages.pillow
-      pythonPackages.sqlite3 pythonPackages.netifaces pythonPackages.apsw
-      pythonPackages.cssselect
-    ];
+  buildInputs = [
+    python pyqt5 sip poppler_utils libpng imagemagick libjpeg
+    fontconfig podofo qtbase chmlib icu sqlite libusb1 libmtp xdg_utils
+  ] ++ (with pythonPackages; [
+    apsw beautifulsoup cssselect cssutils dateutil lxml mechanize netifaces pillow sqlite3
+    # the following are distributed with calibre, but we use upstream instead
+    chardet cherrypy html5lib odfpy routes
+  ]);
 
   installPhase = ''
     export HOME=$TMPDIR/fakehome
diff --git a/pkgs/applications/misc/calibre/no_updates_dialog.patch b/pkgs/applications/misc/calibre/no_updates_dialog.patch
deleted file mode 100644
index 52364f64dac7..000000000000
--- a/pkgs/applications/misc/calibre/no_updates_dialog.patch
+++ /dev/null
@@ -1,16 +0,0 @@
-# Description: Disable update check by default.
-Index: calibre/src/calibre/gui2/main.py
-===================================================================
---- calibre.orig/src/calibre/gui2/main.py	2014-02-02 10:41:28.470954623 +0100
-+++ calibre/src/calibre/gui2/main.py	2014-02-02 10:41:56.546954247 +0100
-@@ -37,8 +37,8 @@
-                       help=_('Start minimized to system tray.'))
-     parser.add_option('-v', '--verbose', default=0, action='count',
-                       help=_('Ignored, do not use. Present only for legacy reasons'))
--    parser.add_option('--no-update-check', default=False, action='store_true',
--            help=_('Do not check for updates'))
-+    parser.add_option('--update-check', dest='no_update_check', default=True, action='store_false',
-+            help=_('Check for updates'))
-     parser.add_option('--ignore-plugins', default=False, action='store_true',
-             help=_('Ignore custom plugins, useful if you installed a plugin'
-                 ' that is preventing calibre from starting'))
diff --git a/pkgs/top-level/all-packages.nix b/pkgs/top-level/all-packages.nix
index eb2e5b8decf6..2e6dc1f8b023 100644
--- a/pkgs/top-level/all-packages.nix
+++ b/pkgs/top-level/all-packages.nix
@@ -12527,7 +12527,7 @@ in
 
   calcurse = callPackage ../applications/misc/calcurse { };
 
-  calibre = qt55.callPackage ../applications/misc/calibre {
+  calibre = qt5.callPackage ../applications/misc/calibre {
     inherit (pythonPackages) pyqt5 sip;
   };