diff --git a/pkgs/applications/virtualization/virtualbox/default.nix b/pkgs/applications/virtualization/virtualbox/default.nix
index 8bcf122132e..161e3ab35bd 100644
--- a/pkgs/applications/virtualization/virtualbox/default.nix
+++ b/pkgs/applications/virtualization/virtualbox/default.nix
@@ -1,6 +1,6 @@
-{ stdenv, fetchurl, lib, iasl, dev86, pam, libxslt, libxml2, libX11, xproto, libXext
-, libXcursor, libXmu, qt4, libIDL, SDL, libcap, zlib, libpng, glib, kernel, lvm2
-, libXrandr
+{ stdenv, buildEnv, fetchurl, lib, iasl, dev86, pam, libxslt, libxml2, libX11, xproto, libXext
+, libXcursor, libXmu, qt5, libIDL, SDL, libcap, zlib, libpng, glib, kernel, lvm2
+, libXrandr, libXinerama
 , which, alsaLib, curl, libvpx, gawk, nettools, dbus
 , xorriso, makeself, perl, pkgconfig, nukeReferences
 , javaBindings ? false, jdk ? null
@@ -20,7 +20,7 @@ let
   # revision/hash as well. See
   # http://download.virtualbox.org/virtualbox/${version}/SHA256SUMS
   # for hashes.
-  version = "5.0.26";
+  version = "5.1.4";
 
   forEachModule = action: ''
     for mod in \
@@ -41,12 +41,12 @@ let
   '';
 
   # See https://github.com/NixOS/nixpkgs/issues/672 for details
-  extpackRevision = "108824";
+  extpackRevision = "110228";
   extensionPack = requireFile rec {
     name = "Oracle_VM_VirtualBox_Extension_Pack-${version}-${extpackRevision}.vbox-extpack";
     # IMPORTANT: Hash must be base16 encoded because it's used as an input to
     # VBoxExtPackHelperApp!
-    sha256 = "2f2302c7ba3d00a1258fe8e7767a6eb08dccdc3c31f6e3eeb74063c2c268b104";
+    sha256 = "9462ff1b567c37ad9a33c0c7ca1925776615ec89b5a72563f29a8cc8514cf316";
     message = ''
       In order to use the extension pack, you need to comply with the VirtualBox Personal Use
       and Evaluation License (PUEL) available at:
@@ -60,23 +60,28 @@ let
     '';
   };
 
+  vbox-qt5-env = buildEnv {
+    name = "vbox-qt5-env-${version}";
+    paths = [ qt5.qtbase.dev qt5.qtbase.out qt5.qtx11extras.dev qt5.qtx11extras.out qt5.qttools.dev ];
+  };
+
 in stdenv.mkDerivation {
   name = "virtualbox-${version}-${kernel.version}";
 
   src = fetchurl {
     url = "http://download.virtualbox.org/virtualbox/${version}/VirtualBox-${version}.tar.bz2";
-    sha256 = "78dec1369d2c8feefea3c682d95e76c0e99414c56626388035cf4061d4dad62e";
+    sha256 = "b9a14a7771059c55c44b97f8d4eef9bea84544f3e215e0caa563bc35e2f16aaf";
   };
 
   buildInputs =
     [ iasl dev86 libxslt libxml2 xproto libX11 libXext libXcursor libIDL
       libcap glib lvm2 python alsaLib curl libvpx pam xorriso makeself perl
-      pkgconfig which libXmu nukeReferences ]
+      pkgconfig which libXmu nukeReferences libpng ]
     ++ optional javaBindings jdk
     ++ optional pythonBindings python
     ++ optional pulseSupport libpulseaudio
-    ++ optionals (headless) [ libXrandr libpng ]
-    ++ optionals (!headless) [ qt4 SDL ];
+    ++ optionals (headless) [ libXrandr ]
+    ++ optionals (!headless) [ vbox-qt5-env libXinerama SDL ];
 
   hardeningDisable = [ "fortify" "pic" "stackprotector" ];
 
@@ -103,11 +108,12 @@ in stdenv.mkDerivation {
     set +x
   '';
 
-  patches = optional enableHardening ./hardened.patch;
+  patches = optional enableHardening ./hardened.patch
+    ++ [ ./libressl.patch ];
 
   postPatch = ''
     sed -i -e 's|/sbin/ifconfig|${nettools}/bin/ifconfig|' \
-      src/apps/adpctl/VBoxNetAdpCtl.cpp
+      src/VBox/HostDrivers/adpctl/VBoxNetAdpCtl.cpp
   '';
 
   # first line: ugly hack, and it isn't yet clear why it's a problem
@@ -135,7 +141,7 @@ in stdenv.mkDerivation {
 
     ./configure \
       ${optionalString headless "--build-headless"} \
-      ${optionalString (!headless) "--with-qt4-dir=${qt4}"} \
+      ${optionalString (!headless) "--with-qt-dir=${vbox-qt5-env}"} \
       ${optionalString (!javaBindings) "--disable-java"} \
       ${optionalString (!pythonBindings) "--disable-python"} \
       ${optionalString (!pulseSupport) "--disable-pulse"} \
diff --git a/pkgs/applications/virtualization/virtualbox/guest-additions/default.nix b/pkgs/applications/virtualization/virtualbox/guest-additions/default.nix
index 56e02519792..0a6293462b8 100644
--- a/pkgs/applications/virtualization/virtualbox/guest-additions/default.nix
+++ b/pkgs/applications/virtualization/virtualbox/guest-additions/default.nix
@@ -12,7 +12,7 @@ stdenv.mkDerivation {
 
   src = fetchurl {
     url = "http://download.virtualbox.org/virtualbox/${version}/VBoxGuestAdditions_${version}.iso";
-    sha256 = "7458ee5a7121a7d243fd6a7528ba427945d9120c5efc7cd75b3951fb01f09c59";
+    sha256 = "e385b698338003595f6cdeee7b631ec6713058ba1227d1f2a1da342bdf741982";
   };
 
   KERN_DIR = "${kernel.dev}/lib/modules/*/build";
diff --git a/pkgs/applications/virtualization/virtualbox/libressl.patch b/pkgs/applications/virtualization/virtualbox/libressl.patch
new file mode 100644
index 00000000000..db9b7e7a59d
--- /dev/null
+++ b/pkgs/applications/virtualization/virtualbox/libressl.patch
@@ -0,0 +1,47 @@
+diff --git a/src/VBox/Runtime/common/crypto/digest-builtin.cpp b/src/VBox/Runtime/common/crypto/digest-builtin.cpp
+index 66b4304..1aaceff 100644
+--- a/src/VBox/Runtime/common/crypto/digest-builtin.cpp
++++ b/src/VBox/Runtime/common/crypto/digest-builtin.cpp
+@@ -561,7 +561,7 @@ static PCRTCRDIGESTDESC const g_apDigestOps[] =
+  * OpenSSL EVP.
+  */
+ 
+-# if OPENSSL_VERSION_NUMBER >= 0x10100000
++# if OPENSSL_VERSION_NUMBER >= 0x10100000 && !defined(LIBRESSL_VERSION_NUMBER)
+ /** @impl_interface_method{RTCRDIGESTDESC::pfnNew} */
+ static DECLCALLBACK(void*) rtCrDigestOsslEvp_New(void)
+ {
+@@ -597,7 +597,7 @@ static DECLCALLBACK(int) rtCrDigestOsslEvp_Init(void *pvState, void *pvOpaque, b
+     if (fReInit)
+     {
+         pEvpType = EVP_MD_CTX_md(pThis);
+-# if OPENSSL_VERSION_NUMBER >= 0x10100000
++# if OPENSSL_VERSION_NUMBER >= 0x10100000 && !defined(LIBRESSL_VERSION_NUMBER)
+         EVP_MD_CTX_reset(pThis);
+ # else
+         EVP_MD_CTX_cleanup(pThis);
+@@ -616,7 +616,7 @@ static DECLCALLBACK(int) rtCrDigestOsslEvp_Init(void *pvState, void *pvOpaque, b
+ static DECLCALLBACK(void) rtCrDigestOsslEvp_Delete(void *pvState)
+ {
+     EVP_MD_CTX *pThis = (EVP_MD_CTX *)pvState;
+-# if OPENSSL_VERSION_NUMBER >= 0x10100000
++# if OPENSSL_VERSION_NUMBER >= 0x10100000 && !defined(LIBRESSL_VERSION_NUMBER)
+     EVP_MD_CTX_reset(pThis);
+ # else
+     EVP_MD_CTX_cleanup(pThis);
+@@ -661,13 +661,13 @@ static RTCRDIGESTDESC const g_rtCrDigestOpenSslDesc =
+     NULL,
+     RTDIGESTTYPE_UNKNOWN,
+     EVP_MAX_MD_SIZE,
+-# if OPENSSL_VERSION_NUMBER >= 0x10100000
++# if OPENSSL_VERSION_NUMBER >= 0x10100000 && !defined(LIBRESSL_VERSION_NUMBER)
+     0,
+ # else
+     sizeof(EVP_MD_CTX),
+ # endif
+     0,
+-# if OPENSSL_VERSION_NUMBER >= 0x10100000
++# if OPENSSL_VERSION_NUMBER >= 0x10100000 && !defined(LIBRESSL_VERSION_NUMBER)
+     rtCrDigestOsslEvp_New,
+     rtCrDigestOsslEvp_Free,
+ # else