Another test, this time in an amd64 virtualbox VM. I installed all the wine1.6 packages, enabled jre's PPA, apt-get dist-upgrade then apt-get autoremove. At each step, I ran some applications in wine. $ sudo apt-get install wine wine1.4 wine1.4-amd64 wine1.4-dbg wine1.4-dev wine1.4-i386 wine1.6 wine1.6-amd64 wine1.6-dbg wine1.6-dev wine1.6-i386 Reading package lists... Done Building dependency tree Reading state information... Done The following additional packages will be installed: binfmt-support cabextract fonts-horai-umefont fonts-unfonts-core fonts-wqy-microhei gcc-6-base:i386 gnome-exe-thumbnailer icoutils libasn1-8-heimdal:i386 libasound2:i386 libasound2-plugins:i386 libasyncns0:i386 libavahi-client3:i386 libavahi-common-data:i386 libavahi-common3:i386 libbsd0:i386 libc6:i386 libcapi20-3 libcapi20-3:i386 libcomerr2:i386 libcups2:i386 libdb5.3:i386 libdbus-1-3:i386 libdrm-amdgpu1:i386 libdrm-intel1:i386 libdrm-nouveau2:i386 libdrm-radeon1:i386 libdrm2:i386 libedit2:i386 libelf1:i386 libexif12:i386 libexpat1:i386 libffi6:i386 libflac8:i386 libfontconfig1:i386 libfreetype6:i386 libgcc1:i386 libgcrypt20:i386 libgd3:i386 libgif7 libgif7:i386 libgl1-mesa-dri:i386 libgl1-mesa-glx:i386 libglapi-mesa:i386 libglu1-mesa:i386 libgmp10:i386 libgnutls30:i386 libgpg-error0:i386 libgphoto2-6:i386 libgphoto2-port12:i386 libgpm2:i386 libgssapi-krb5-2:i386 libgssapi3-heimdal:i386 libhcrypto4-heimdal:i386 libheimbase1-heimdal:i386 libheimntlm0-heimdal:i386 libhogweed4:i386 libhx509-5-heimdal:i386 libice6:i386 libicu57:i386 libidn11:i386 libieee1284-3:i386 libjack-jackd2-0:i386 libjbig0:i386 libjpeg-turbo8:i386 libjpeg8:i386 libjson-c3:i386 libk5crypto3:i386 libkeyutils1:i386 libkrb5-26-heimdal:i386 libkrb5-3:i386 libkrb5support0:i386 liblcms2-2:i386 libldap-2.4-2:i386 libllvm3.8:i386 libltdl7:i386 liblzma5:i386 libmpg123-0 libmpg123-0:i386 libmspack0 libncurses5:i386 libnettle6:i386 libodbc1 libogg0:i386 libopenal-data libopenal1 libopenal1:i386 libosmesa6 libosmesa6:i386 libp11-kit-gnome-keyring:i386 libp11-kit0:i386 libpciaccess0:i386 libpcre3:i386 libpng16-16:i386 libpulse0:i386 libroken18-heimdal:i386 libsamplerate0:i386 libsane:i386 libsasl2-2:i386 libsasl2-modules:i386 libsasl2-modules-db:i386 libselinux1:i386 libsm6:i386 libsndfile1:i386 libspeexdsp1:i386 libsqlite3-0:i386 libssl1.0.0:i386 libstdc++6:i386 libsystemd0:i386 libtasn1-6:i386 libtiff5:i386 libtinfo5:i386 libtxc-dxtn-s2tc0:i386 libudev1:i386 libusb-1.0-0:i386 libuuid1:i386 libv4l-0:i386 libv4lconvert0:i386 libvorbis0a:i386 libvorbisenc2:i386 libwebp6:i386 libwind0-heimdal:i386 libwrap0:i386 libx11-6:i386 libx11-xcb1:i386 libxau6:i386 libxcb-dri2-0:i386 libxcb-dri3-0:i386 libxcb-glx0:i386 libxcb-present0:i386 libxcb-sync1:i386 libxcb1:i386 libxcomposite1:i386 libxcursor1:i386 libxdamage1:i386 libxdmcp6:i386 libxext6:i386 libxfixes3:i386 libxi6:i386 libxinerama1:i386 libxml2:i386 libxpm4:i386 libxrandr2:i386 libxrender1:i386 libxshmfence1:i386 libxslt1.1:i386 libxt6:i386 libxxf86vm1:i386 ocl-icd-libopencl1 ocl-icd-libopencl1:i386 odbcinst odbcinst1debian2 p11-kit-modules:i386 p7zip ttf-mscorefonts-installer ttf-wqy-microhei unixodbc wine-gecko2.21 wine-gecko2.21:i386 wine-mono0.0.8 winetricks zlib1g:i386 Suggested packages: libterm-readline-gnu-perl | libterm-readline-perl-perl glibc-doc:i386 locales:i386 isdnutils-doc isdnutils-doc:i386 rng-tools:i386 libgd-tools:i386 gnutls-bin:i386 gphoto2:i386 gpm:i386 krb5-doc:i386 krb5-user:i386 jackd2:i386 libmyodbc odbc-postgresql tdsodbc unixodbc-bin libportaudio2:i386 hplip:i386 libsane-extras:i386 libsasl2-modules-otp:i386 libsasl2-modules-ldap:i386 libsasl2-modules-sql:i386 libsasl2-modules-gssapi-mit:i386 | libsasl2-modules-gssapi-heimdal:i386 opencl-icd opencl-icd:i386 p7zip-full dosbox:any winbind aria2 tor Recommended packages: xml-core:i386 fonts-droid The following NEW packages will be installed: binfmt-support cabextract fonts-horai-umefont fonts-unfonts-core fonts-wqy-microhei gcc-6-base:i386 gnome-exe-thumbnailer icoutils libasn1-8-heimdal:i386 libasound2:i386 libasound2-plugins:i386 libasyncns0:i386 libavahi-client3:i386 libavahi-common-data:i386 libavahi-common3:i386 libbsd0:i386 libc6:i386 libcapi20-3 libcapi20-3:i386 libcomerr2:i386 libcups2:i386 libdb5.3:i386 libdbus-1-3:i386 libdrm-amdgpu1:i386 libdrm-intel1:i386 libdrm-nouveau2:i386 libdrm-radeon1:i386 libdrm2:i386 libedit2:i386 libelf1:i386 libexif12:i386 libexpat1:i386 libffi6:i386 libflac8:i386 libfontconfig1:i386 libfreetype6:i386 libgcc1:i386 libgcrypt20:i386 libgd3:i386 libgif7 libgif7:i386 libgl1-mesa-dri:i386 libgl1-mesa-glx:i386 libglapi-mesa:i386 libglu1-mesa:i386 libgmp10:i386 libgnutls30:i386 libgpg-error0:i386 libgphoto2-6:i386 libgphoto2-port12:i386 libgpm2:i386 libgssapi-krb5-2:i386 libgssapi3-heimdal:i386 libhcrypto4-heimdal:i386 libheimbase1-heimdal:i386 libheimntlm0-heimdal:i386 libhogweed4:i386 libhx509-5-heimdal:i386 libice6:i386 libicu57:i386 libidn11:i386 libieee1284-3:i386 libjack-jackd2-0:i386 libjbig0:i386 libjpeg-turbo8:i386 libjpeg8:i386 libjson-c3:i386 libk5crypto3:i386 libkeyutils1:i386 libkrb5-26-heimdal:i386 libkrb5-3:i386 libkrb5support0:i386 liblcms2-2:i386 libldap-2.4-2:i386 libllvm3.8:i386 libltdl7:i386 liblzma5:i386 libmpg123-0 libmpg123-0:i386 libmspack0 libncurses5:i386 libnettle6:i386 libodbc1 libogg0:i386 libopenal-data libopenal1 libopenal1:i386 libosmesa6 libosmesa6:i386 libp11-kit-gnome-keyring:i386 libp11-kit0:i386 libpciaccess0:i386 libpcre3:i386 libpng16-16:i386 libpulse0:i386 libroken18-heimdal:i386 libsamplerate0:i386 libsane:i386 libsasl2-2:i386 libsasl2-modules:i386 libsasl2-modules-db:i386 libselinux1:i386 libsm6:i386 libsndfile1:i386 libspeexdsp1:i386 libsqlite3-0:i386 libssl1.0.0:i386 libstdc++6:i386 libsystemd0:i386 libtasn1-6:i386 libtiff5:i386 libtinfo5:i386 libtxc-dxtn-s2tc0:i386 libudev1:i386 libusb-1.0-0:i386 libuuid1:i386 libv4l-0:i386 libv4lconvert0:i386 libvorbis0a:i386 libvorbisenc2:i386 libwebp6:i386 libwind0-heimdal:i386 libwrap0:i386 libx11-6:i386 libx11-xcb1:i386 libxau6:i386 libxcb-dri2-0:i386 libxcb-dri3-0:i386 libxcb-glx0:i386 libxcb-present0:i386 libxcb-sync1:i386 libxcb1:i386 libxcomposite1:i386 libxcursor1:i386 libxdamage1:i386 libxdmcp6:i386 libxext6:i386 libxfixes3:i386 libxi6:i386 libxinerama1:i386 libxml2:i386 libxpm4:i386 libxrandr2:i386 libxrender1:i386 libxshmfence1:i386 libxslt1.1:i386 libxt6:i386 libxxf86vm1:i386 ocl-icd-libopencl1 ocl-icd-libopencl1:i386 odbcinst odbcinst1debian2 p11-kit-modules:i386 p7zip ttf-mscorefonts-installer ttf-wqy-microhei unixodbc wine wine-gecko2.21 wine-gecko2.21:i386 wine-mono0.0.8 wine1.4 wine1.4-amd64 wine1.4-dbg wine1.4-dev wine1.4-i386:i386 wine1.6 wine1.6-amd64 wine1.6-dbg wine1.6-dev wine1.6-i386:i386 winetricks zlib1g:i386 0 upgraded, 173 newly installed, 0 to remove and 0 not upgraded. Need to get 237 MB of archives. After this operation, 831 MB of additional disk space will be used. Do you want to continue? [Y/n] $ sudo add-apt-repository ppa:jre-phoenix/transition+wine1.6+wine $ sudo apt-get update $ sudo apt-get dist-upgrade Reading package lists... Done Building dependency tree Reading state information... Done Calculating upgrade... Done The following packages were automatically installed and are no longer required: fonts-horai-umefont fonts-unfonts-core fonts-wqy-microhei gnome-exe-thumbnailer icoutils libcapi20-3 libcapi20-3:i386 libexif12:i386 libgd3:i386 libgif7 libgif7:i386 libgphoto2-6:i386 libgphoto2-port12:i386 libice6:i386 libieee1284-3:i386 libp11-kit-gnome-keyring:i386 libsane:i386 libsm6:i386 libusb-1.0-0:i386 libv4l-0:i386 libv4lconvert0:i386 libwebp6:i386 libxpm4:i386 libxt6:i386 odbcinst odbcinst1debian2 p11-kit-modules:i386 ttf-wqy-microhei unixodbc wine-gecko2.21 wine-gecko2.21:i386 wine-mono0.0.8 wine1.6 wine1.6-amd64 wine1.6-dev wine1.6-i386:i386 Use 'sudo apt autoremove' to remove them. The following packages will be REMOVED: wine wine1.4 wine1.4-amd64 wine1.4-dbg wine1.4-dev wine1.4-i386:i386 wine1.6-dbg The following NEW packages will be installed: fonts-wine libgettextpo0 libgsm1 libgsm1:i386 libodbc1:i386 libpcap0.8:i386 libwine libwine:i386 libwine-dev wine-stable wine32:i386 wine64 wine64-tools The following packages will be upgraded: wine1.6 wine1.6-amd64 wine1.6-dev wine1.6-i386:i386 4 upgraded, 13 newly installed, 7 to remove and 0 not upgraded. Need to get 40.7 MB of archives. After this operation, 9,913 kB of additional disk space will be used. Do you want to continue? [Y/n] $ sudo apt-get autoremove Reading package lists... Done Building dependency tree Reading state information... Done The following packages will be REMOVED: fonts-horai-umefont fonts-unfonts-core fonts-wqy-microhei gnome-exe-thumbnailer icoutils libcapi20-3 libcapi20-3:i386 libexif12:i386 libgd3:i386 libgif7 libgif7:i386 libgphoto2-6:i386 libgphoto2-port12:i386 libice6:i386 libieee1284-3:i386 libp11-kit-gnome-keyring:i386 libsane:i386 libsm6:i386 libusb-1.0-0:i386 libv4l-0:i386 libv4lconvert0:i386 libwebp6:i386 libxpm4:i386 libxt6:i386 odbcinst odbcinst1debian2 p11-kit-modules:i386 ttf-wqy-microhei unixodbc wine-gecko2.21 wine-gecko2.21:i386 wine-mono0.0.8 wine1.6 wine1.6-amd64 wine1.6-dev wine1.6-i386:i386 0 upgraded, 0 newly installed, 36 to remove and 0 not upgraded. After this operation, 233 MB disk space will be freed. Do you want to continue? [Y/n]