Your sources.list file entry looks incorrect.  I would definitely not recommend using trust=yes for a repo like tor, as it bypasses apt's security checks.

According to the instructions you linked <https://support.torproject.org/apt/tor-deb-repo/>, your source for the tor packages should be listed in /etc/apt/sources.list.d/tor.list as something like:

deb [signed-by=/usr/share/keyrings/tor-archive-keyring.gpg] https://deb.torproject.org/torproject.org buster main deb-src [signed-by=/usr/share/keyrings/tor-archive-keyring.gpg] https://deb.torproject.org/torproject.org buster main

The instructions tell you how to import the repo key as well:


# wget -qO- https://deb.torproject.org/torproject.org/A3C4F0F979CAA22CDBA8F512EE8CBC9E886DDD89.asc | gpg --dearmor | tee /usr/share/keyrings/tor-archive-keyring.gpg >/dev/null



On 5/3/22 13:10, Keifer Bly wrote:
I am not sure how to get rid of the trusty / ubuntu packages? I simply followed the instructions here:

https://support.torproject.org/apt/tor-deb-repo/

Thanks.
--Keifer


On Mon, May 2, 2022 at 10:31 PM Keifer Bly <[email protected]> wrote:

    Hi all,

    So I am running a tor relay on Debian, but no matter what when
    updating tor there is an “updating from such a respiritpry can’t
    be done securely and is therefore disabled by default”. Here is
    the log

    Get:1 http://security.debian.org buster/updates InRelease [65.4 kB]

    Hit:2 http://deb.debian.org/debian buster InRelease

    Get:3 http://deb.debian.org/debian buster-updates InRelease [51.9 kB]

    Get:4 http://deb.debian.org/debian buster-backports InRelease
    [46.7 kB]

    Ign:5 http://ftp.de.debian.org/debian stretch InRelease

    Hit:6 http://ftpde.debian.org/debian stretch Release

    Ign:7 http://deb.torproject.org/torproject.org trusty InRelease

    Ign:8 http://deb.torproject.org/torproject.org trusty Release

    Ign:9 http://deb.torproject.org/torproject.org trusty/main Sources

    Ign:10 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:11 http://deb.torproject.org/torproject.org trusty/main amd64
    Packages

    Ign:12 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Ign:13 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Ign:9 http://deb.torproject.org/torproject.org trusty/main Sources

    Ign:10 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:11 http://deb.torproject.org/torproject.org trusty/main amd64
    Packages

    Ign:12 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Ign:13 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Ign:14 https://deb.torproject.org/torproject.org amd64 InRelease

    Ign:9 http://deb.torproject.org/torproject.org trusty/main Sources

    Ign:10 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:11 http://deb.torproject.org/torproject.org trusty/main amd64
    Packages

    Ign:12 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Ign:13 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Err:15 https://deb.torproject.org/torproject.org amd64 Release

      Certificate verification failed: The certificate is NOT trusted.
    The certificate chain uses expired certificate.  Could not
    handshake: Error in the certificate verification. [IP:
    95.216.163.36 443]

    Ign:9 http://deb.torproject.org/torproject.org trusty/main Sources

    Ign:10 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:11 http://deb.torproject.org/torproject.org trusty/main amd64
    Packages

    Ign:12 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Ign:13 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Ign:9 http://deb.torproject.org/torproject.org trusty/main Sources

    Ign:10 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:11 http://deb.torproject.org/torproject.org trusty/main amd64
    Packages

    Ign:12 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Ign:13 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Ign:9 http://deb.torproject.org/torproject.org trusty/main Sources

    Ign:10 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:11 http://deb.torproject.org/torproject.org trusty/main amd64
    Packages

    Ign:12 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Ign:13 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Err:9 http://deb.torproject.org/torproject.org trusty/main Sources

      404  Not Found [IP: 116.202.120.166 80]

    Ign:10 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:11 http://deb.torproject.org/torproject.org trusty/main amd64
    Packages

    Ign:12 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Ign:13 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Reading package lists... Done

    N: Ignoring file 'DEADJOE' in directory '/etc/apt/sources.list.d/'
    as it has no filename extension

    E: The repository 'https://deb.torproject.org/torproject.org amd64
    Release' does not have a Release file.

    N: Updating from such a repository can't be done securely, and is
    therefore disabled by default.

    N: See apt-secure(8) manpage for repository creation and user
    configuration details.

    root@vps-3e661acc:/home/debian# nano /etc/apt/sources.list

    root@vps-3e661acc:/home/debian# nano /etc/apt/sources.list

    root@vps-3e661acc:/home/debian# apt-get update

    Hit:1 http://security.debian.org buster/updates InRelease

    Hit:2 http://deb.debian.org/debian buster InRelease

    Hit:3 http://deb.debian.org/debian buster-updates InRelease

    Hit:4 http://deb.debian.org/debian buster-backports InRelease

    Ign:5 https://deb.torproject.org/torproject.org amd64 InRelease

    Ign:6 http://ftp.de.debian.org/debian stretch InRelease

    Ign:7 http://deb.torproject.org/torproject.org trusty InRelease

    Hit:8 http://ftp.de.debian.org/debian stretch Release

    Ign:9 http://deb.torproject.org/torproject.org trusty Release

    Err:10 https://deb.torproject.org/torproject.org amd64 Release

      Certificate verification failed: The certificate is NOT trusted.
    The certificate chain uses expired certificate.  Could not
    handshake: Error in the certificate verification. [IP:
    116.202.120.165 443]

    Ign:11 http://deb.torproject.org/torproject.org trusty/main Sources

    Ign:12 http://deb.torproject.org/torproject.org trusty/main amd64
    Packages

    Ign:13 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:14 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Ign:15 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Ign:11 http://deb.torproject.org/torproject.org trusty/main Sources

    Ign:12 http://deb.torproject.org/torproject.org trusty/main amd64
    Packages

    Ign:13 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:14 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Ign:15 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Ign:11 http://deb.torproject.org/torproject.org trusty/main Sources

    Ign:12 http://deb.torproject.org/torproject.org trusty/main amd64
    Packages

    Ign:13 http://deb.torproject.org/torprojectorg trusty/main all
    Packages

    Ign:14 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Ign:15 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Ign:11 http://deb.torproject.org/torproject.org trusty/main Sources

    Ign:12 http://deb.torprojectorg/torproject.org trusty/main amd64
    Packages

    Ign:13 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:14 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Ign:15 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Ign:11 http://deb.torproject.org/torproject.org trusty/main Sources

    Ign:12 http://deb.torproject.org/torproject.org trusty/main amd64
    Packages

    Ign:13 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:14 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Ign:15 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Ign:11 http://deb.torproject.org/torproject.org trusty/main Sources

    Ign:12 http://deb.torproject.org/torproject.org trusty/main amd64
    Packages

    Ign:13 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:14 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Ign:15 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Err:11 http://deb.torproject.org/torproject.org trusty/main Sources

      404  Not Found [IP: 95.216.163.36 80]

    Ign:12 http://deb.torproject.org/torproject.org trusty/main amd64
    Packages

    Ign:13 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:14 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Ign:15 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Reading package lists... Done

    N: Ignoring file 'DEADJOE' in directory '/etc/apt/sourceslist.d/'
    as it has no filename extension

    E: The repository 'https://deb.torproject.org/torproject.org amd64
    Release' does not have a Release file.

    N: Updating from such a repository can't be done securely, and is
    therefore disabled by default.

    N: See apt-secure(8) manpage for repository creation and user
    configuration details.

    root@vps-3e661acc:/home/debian# tor

    May 03 05:20:21.468 [notice] Tor 0.4.5.10 running on Linux with
    Libevent 2.1.8-stable, OpenSSL 1.1.1d, Zlib 1.2.11, Liblzma 5.2.4,
    Libzstd 1.3.8 and Glibc 2.28 as libc.

    May 03 05:20:21.469 [notice] Tor can't help you if you use it
    wrong! Learn how to be safe at
    https://www.torproject.org/download/download#warning

    May 03 05:20:21.469 [notice] Read configuration file "/etc/tor/torrc".

    May 03 05:20:21.470 [notice] Based on detected system memory,
    MaxMemInQueues is set to 1462 MB. You can override this by setting
    MaxMemInQueues by hand.

    May 03 05:20:21.472 [notice] Opening Control listener on
    127.0.0.1:9051 <http://127.0.0.1:9051>

    May 03 05:20:21.472 [notice] Opened Control listener connection
    (ready) on 127.0.0.1:9051 <http://127.0.0.1:9051>

    May 03 05:20:21.472 [notice] Opening OR listener on 0.0.0.0:9001
    <http://0.0.0.0:9001>

    May 03 05:20:21.472 [notice] Opened OR listener connection (ready)
    on 0.0.0.0:9001 <http://0.0.0.0:9001>

    May 03 05:20:21.472 [notice] Opening OR listener on [::]:9001

    May 03 05:20:21.472 [notice] Opened OR listener connection (ready)
    on [::]:9001

    May 03 05:20:21.472 [notice] Opening Directory listener on
    0.0.0.0:9030 <http://0.0.0.0:9030>

    May 03 05:20:21.472 [notice] Opened Directory listener connection
    (ready) on 0.0.0.0:9030 <http://0.0.0.0:9030>

    root@vps-3e661acc:/home/debian# sudo apt update && sudo apt
    install -y --only-upgrade tor

    Hit:1 http://security.debian.org buster/updates InRelease

    Hit:2 http://deb.debian.org/debian buster InRelease

    Hit:3 http://deb.debian.org/debian buster-updates InRelease

    Hit:4 http://deb.debian.org/debian buster-backports InRelease

    Ign:5 http://ftp.de.debian.org/debian stretch InRelease

    Hit:6 http://ftp.de.debian.org/debian stretch Release

    Ign:7 https://deb.torproject.org/torproject.org amd64 InRelease

    Ign:8 http://deb.torproject.org/torproject.org trusty InRelease

    Ign:9 http://deb.torproject.org/torproject.org trusty Release

    Err:10 https://deb.torproject.org/torproject.org amd64 Release

      Certificate verification failed: The certificate is NOT trusted.
    The certificate chain uses expired certificate.  Could not
    handshake: Error in the certificate verification. [IP:
    116.202.120.165 443]

    Ign:11 http://deb.torproject.org/torproject.org trusty/main Sources

    Ign:12 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:13 http://deb.torproject.org/torproject.org trusty/main amd64
    Packages

    Ign:14 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Ign:15 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Ign:11 http://deb.torproject.org/torproject.org trusty/main Sources

    Ign:12 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:13 http://debtorproject.org/torproject.org trusty/main amd64
    Packages

    Ign:14 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Ign:15 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Ign:11 http://debtorproject.org/torproject.org trusty/main Sources

    Ign:12 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:13 http://deb.torproject.org/torproject.org trusty/main amd64
    Packages

    Ign:14 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Ign:15 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Ign:11 http://deb.torproject.org/torproject.org trusty/main Sources

    Ign:12 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:13 http://deb.torproject.org/torproject.org trusty/main amd64
    Packages

    Ign:14 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Ign:15 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Ign:11 http://deb.torproject.org/torproject.org trusty/main Sources

    Ign:12 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:13 http://deb.torproject.org/torproject.org trusty/main amd64
    Packages

    Ign:14 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Ign:15 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Ign:11 http://deb.torproject.org/torproject.org trusty/main Sources

    Ign:12 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:13 http://deb.torproject.org/torproject.org trusty/main amd64
    Packages

    Ign:14 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Ign:15 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Err:11 http://deb.torproject.org/torproject.org trusty/main Sources

      404  Not Found [IP: 95.216.163.36 80]

    Ign:12 http://deb.torproject.org/torproject.org trusty/main all
    Packages

    Ign:13 http://deb.torproject.org/torproject.org trusty/main amd64
    Packages

    Ign:14 http://deb.torproject.org/torproject.org trusty/main
    Translation-en

    Ign:15 http://deb.torproject.org/torproject.org trusty/main
    Translation-en_US

    Reading package lists... Done

    N: Ignoring file 'DEADJOE' in directory '/etc/apt/sources.list.d/'
    as it has no filename extension

    E: The repository 'https://deb.torproject.org/torproject.org amd64
    Release' does not have a Release file.

    N: Updating from such a repository can't be done securely, and is
    therefore disabled by default.

    N: See apt-secure(8) manpage for repository creation and user
    configuration details.

    This happens despite tor being listed as trsuted in my sources file:

    ## Note, this file is written by cloud-init on first boot of an
    instance

    ## modifications made here will not survive a re-bundle.

    ## if you wish to make changes you can:

    ## a.) add 'apt_preserve_sources_list: true' to /etc/cloud/cloud.cfg

    ##     or do the same in user-data

    ## b.) add sources in /etc/apt/sources.list.d

    ## c.) make changes to template file
    /etc/cloud/templates/sources.list.debian.tmpl

    ###

    # See
    http://www.debianorg/releases/stable/i386/release-notes/ch-upgrading.html

    # for how to upgrade to newer versions of the distribution.

    deb http://deb.debian.org/debian buster main

    deb-src http://deb.debian.org/debian buster main

    ## Major bug fix updates produced after the final release of the

    ## distribution.

    deb http://security.debian.org/ buster/updates main

    deb-src http://security.debian.org/ buster/updates main

    deb [trusted=yes] http://deb.debian.org/debian buster-updates main

    deb-src [trusted=yes] http://deb.debian.org/debian buster-updates main

    ## Uncomment the following two lines to add software from the
    'backports'

    ## repository.

    ##

    ## N.B. software from this repository may not have been tested as

    ## extensively as that contained in the main release, although it
    includes

    ## newer versions of some applications which may provide useful
    features.

    deb http://deb.debian.org/debian buster-backports main

    deb-src http://deb.debian.org/debian buster-backports main

    deb http://ftp.de.debian.org/debian stretch main

    deb [trusted=yes] http://deb.torproject.org/torproject.org trusty main

    deb-src [trusted=yes] http://deb.torproject.org/torproject.org
    trusty main

    So, for some reason Debian is seeing tor as untrusted despite that
    it has been listed as trusted. Tor is being run as root so its not
    a restricted user error. I am wondering why this might be
    happening? Thanks.

    --Keifer


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