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Automatic install of additional software fails because Tails has not yet connected to Tor

Sometimes Tails (v4.0) fails to automatically install the additional software I have selected for automatic installation.

I believe the install fails because Tails has not yet connected to Tor when the additional software is attempted to be installed. (I am displayed the “Tor is ready” notification only after the install fails.)

N.B. I encounter no problems installing the additional software with apt after Tails has connected to Tor.

Here is the log I am given after the install fails:

[INFO] Starting to install additional software...
[INFO] Found additional packages list.
[WARNING] Found a copy of old APT lists, restoring it.
[INFO] Will install the following packages: fonts-powerline po4a vim-nox powerline ikiwiki python3-powerline perlmagick libyaml-syck-perl vim-addon-manager
[INFO] Reading package lists...
[INFO] Building dependency tree...
[INFO] Reading state information...
[INFO] The following package was automatically installed and is no longer required:
[INFO]   libpcre2-posix0
[INFO] Use 'apt autoremove' to remove it.
[INFO] The following additional packages will be installed:
[INFO]   libhtml-scrubber-perl libhtml-template-perl libimage-magick-perl
[INFO]   libimage-magick-q16-perl libjson-perl libmarkdown2 libosp5 libruby2.5
[INFO]   libsgmls-perl libtcl8.6 libtext-markdown-discount-perl libyaml-tiny-perl
[INFO]   opensp rake ruby ruby-did-you-mean ruby-minitest ruby-net-telnet
[INFO]   ruby-power-assert ruby-test-unit ruby-xmlrpc ruby2.5 rubygems-integration
[INFO]   sgml-base vim-runtime
[INFO] Suggested packages:
[INFO]   dvipng graphviz libfile-mimeinfo-perl libhighlight-perl libmagickcore-extra
[INFO]   libmailtools-perl libnet-amazon-s3-perl libnet-inet6glue-perl
[INFO]   libsearch-xapian-perl libsort-naturally-perl libsparkline-php
[INFO]   libtext-csv-perl libtext-multimarkdown-perl libtext-textile-perl
[INFO]   libtext-typography-perl libtext-wikicreole-perl libtext-wikiformat-perl
[INFO]   libxml-feed-perl libxml-writer-perl polygen python3-docutils texlive tidy
[INFO]   viewvc | gitweb | viewcvs xapian-omega libipc-sharedcache-perl
[INFO]   imagemagick-doc sgmlspl sgmls-doc tcl8.6 doc-base sgml-data powerline-doc ri
[INFO]   ruby-dev bundler sgml-base-doc cscope vim-doc
[INFO] Recommended packages:
[INFO]   gcc | c-compiler libauthen-passphrase-perl libc6-dev | libc-dev
[INFO]   libcgi-formbuilder-perl libcgi-session-perl libcrypt-ssleay-perl
[INFO]   libgravatar-url-perl liblwpx-paranoidagent-perl libmail-sendmail-perl
[INFO]   libnet-openid-consumer-perl librpc-xml-perl libterm-readline-gnu-perl
[INFO]   libxml-simple-perl libjson-xs-perl libterm-readkey-perl zip fonts-lato
[INFO] The following NEW packages will be installed:
[INFO]   fonts-powerline ikiwiki libhtml-scrubber-perl libhtml-template-perl
[INFO]   libimage-magick-perl libimage-magick-q16-perl libjson-perl libmarkdown2
[INFO]   libosp5 libruby2.5 libsgmls-perl libtcl8.6 libtext-markdown-discount-perl
[INFO]   libyaml-syck-perl libyaml-tiny-perl opensp perlmagick po4a powerline
[INFO]   python3-powerline rake ruby ruby-did-you-mean ruby-minitest ruby-net-telnet
[INFO]   ruby-power-assert ruby-test-unit ruby-xmlrpc ruby2.5 rubygems-integration
[INFO]   sgml-base vim-addon-manager vim-nox vim-runtime
[INFO] 0 upgraded, 34 newly installed, 0 to remove and 20 not upgraded.
[INFO] Need to get 9156 kB/17.6 MB of archives.
[INFO] After this operation, 70.5 MB of additional disk space will be used.
[INFO] Err:1 tor+http://vwakviie2ienjx6t.onion/debian buster/main amd64 libimage-magick-q16-perl amd64 8:6.9.10.23+dfsg-2.1
[INFO]   Timed out while waiting to read 'first part of response' from proxy socks5h://127.0.0.1:9050 [IP: 127.0.0.1 9050]
[INFO] Get:2 tor+http://vwakviie2ienjx6t.onion/debian buster/main amd64 po4a all 0.55-1 [1542 kB]
[INFO] Get:3 tor+http://vwakviie2ienjx6t.onion/debian buster/main amd64 python3-powerline all 2.7-2 [126 kB]
[INFO] Get:4 tor+http://vwakviie2ienjx6t.onion/debian buster/main amd64 powerline amd64 2.7-2 [51.6 kB]
[INFO] Get:5 tor+http://vwakviie2ienjx6t.onion/debian buster/main amd64 vim-addon-manager all 0.5.10 [19.9 kB]
[INFO] Get:6 tor+http://vwakviie2ienjx6t.onion/debian buster/main amd64 vim-runtime all 2:8.1.0875-5 [5775 kB]
[INFO] Get:7 tor+http://vwakviie2ienjx6t.onion/debian buster/main amd64 vim-nox amd64 2:8.1.0875-5 [1401 kB]
[INFO] Fetched 8866 kB in 1min 14s (120 kB/s)
[INFO] E: Failed to fetch tor+http://vwakviie2ienjx6t.onion/debian/pool/main/i/imagemagick/libimage-magick-q16-perl_6.9.10.23+dfsg-2.1_amd64.deb  Timed out while waiting to read 'first part of response' from proxy socks5h://127.0.0.1:9050 [IP: 127.0.0.1 9050]
[INFO] E: Unable to fetch some archives, maybe run apt-get update or try with --fix-missing?
[WARNING] apt-get exited with returncode 100
[WARNING] Warning: installation of fonts-powerline po4a vim-nox powerline ikiwiki python3-powerline perlmagick libyaml-syck-perl vim-addon-manager failed

Feature Branch: bugfix/17203-upgrade-additional-software-after-tor-has-bootstrapped

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Original created by @cbrownstein on 17203 (Redmine)

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