I still have the same issue. None of the answers above seem to solve it. I have ubuntu 16.04, and I follow the steps described in https://docs.docker.com/install/linux/docker-ce/ubuntu/ I suspect it is related to an apt-get bug regarding https. The information being printed by apt-get is kind of misleading. I think that Failed to fetch.. can also be translated as: problem accessing resource from within an https connection How did I come to this conclusion: First of all I am behind a corporate proxy so I have set the following configuration: /etc/apt/apt.conf Acquire::http::proxy "http://squidproxy:8080/"; Acquire::https::proxy "http://squidproxy:8080/"; Acquire::ftp::proxy "ftp://squidproxy:8080/"; Acquire::https::CaInfo "/etc/ssl/certs/ca-certificates.pem"; /etc/apt/apt.conf.d/99proxy Acquire::http::Proxy { localhost DIRECT; localhost:9020 DIRECT; localhost:9021 DIRECT; }; I performed the following tests with differrent entries in sources.list test entry 1: deb [arch=amd64] https://download.docker.com/linux/ubuntu xenial stable sudo apt-get update W: The repository 'https://download.docker.com/linux/ubuntu xenial Release' does not have a Release file. N: Data from such a repository can't be authenticated and is therefore potentially dangerous to use. N: See apt-secure(8) manpage for repository creation and user configuration details. E: Failed to fetch https://download.docker.com/linux/ubuntu/dists/xenial/stable/binary-amd64/Packages E: Some index files failed to download. They have been ignored, or old ones used instead. Failure test entry 2: deb [arch=amd64] http://localhost:9020/linux/ubuntu xenial stable /etc/apache2/sites-enabled/apt-proxy.conf # http to https reverse proxy configuration. Listen 9020 SSLProxyEngine On # pass from squid proxy ProxyRemote https://download.docker.com/ http://squidproxy:8080 ProxyPass / https://download.docker.com/ ProxyPassReverse / https://download.docker.com/ ErrorLog ${APACHE_LOG_DIR}/apt-proxy-error.log CustomLog ${APACHE_LOG_DIR}/apt-proxy-access.log combined sudo apt-get update Hit:1 .. Hit:2 .. ... Hit:7 http://localhost:9020/linux/ubuntu xenial InRelease Get:8 ... Fetched 323 kB in 0s (419 kB/s) Reading package lists... Done Success test entry 3: deb [arch=amd64] https://localhost:9021/linux/ubuntu xenial stable /etc/apache2/sites-enabled/apt-proxy.conf # https to https revere proxy Listen 9021 # serve on https SSLEngine on SSLCertificateFile /etc/ssl/certs/ssl-cert-snakeoil.pem SSLCertificateKeyFile /etc/ssl/private/ssl-cert-snakeoil.key SSLProxyEngine On # pass from squid proxy ProxyRemote https://download.docker.com/ http://squidproxy:8080 ProxyPass / https://download.docker.com/ ProxyPassReverse / https://download.docker.com/ ErrorLog ${APACHE_LOG_DIR}/apt-proxy-error.log CustomLog ${APACHE_LOG_DIR}/apt-proxy-access.log combined sudo apt-get update W: The repository 'https://localhost:9021/linux/ubuntu xenial Release' does not have a Release file. N: Data from such a repository can't be authenticated and is therefore potentially dangerous to use. N: See apt-secure(8) manpage for repository creation and user configuration details. E: Failed to fetch https://localhost:9021/linux/ubuntu/dists/xenial/stable/binary-amd64/Packages E: Some index files failed to download. They have been ignored, or old ones used instead. Failure In the above cases the url which apt-get Failed to fetch and also the Release file, were actually accessible from browser / wget / curl using the same proxy configuration. The fact that apt-get worked only with http reverse proxy url, implies that there is some issue accessing resources from within an https connection. I do not know what this issue is but apt-get should show a more informative message ( apt is even less verbose ). Note: wiresharking case 1 showed that proxy CONNECT was successful, and no RST was sent, but of course the files could not be read.