Installing Certbot on Debian 8 - OS Package Manager Not Installing Certbot

Greetings,

I’m running into the same issue - backports is enabled, repositories are updated, but certbot fails to install due to the same dependency issues as Dirk experienced.

$ sudo apt-get -t jessie-backports install certbot
Reading package lists... Done
Building dependency tree       
Reading state information... Done
Some packages could not be installed. This may mean that you have
requested an impossible situation or if you are using the unstable
distribution that some required packages have not yet been created
or been moved out of Incoming.
The following information may help to resolve the situation:

The following packages have unmet dependencies:
 certbot : Depends: python-certbot (= 0.9.3-1~bpo8+2) but it is not going to be installed
E: Unable to correct problems, you have held broken packages.

Which leads to…

$ sudo apt-get -t jessie-backports install python-certbot
Reading package lists... Done
Building dependency tree       
Reading state information... Done
Some packages could not be installed. This may mean that you have
requested an impossible situation or if you are using the unstable
distribution that some required packages have not yet been created
or been moved out of Incoming.
The following information may help to resolve the situation:

The following packages have unmet dependencies:
 python-certbot : Depends: python-acme (>= 0.9.3) but it is not going to be installed
E: Unable to correct problems, you have held broken packages.

Which leads to…

$ sudo apt-get -t jessie-backports install python-acme
Reading package lists... Done
Building dependency tree       
Reading state information... Done
The following extra packages will be installed:
  python-cffi-backend python-cryptography python-dnspython python-enum34 python-funcsigs python-idna python-ipaddress python-mock python-ndg-httpsclient python-openssl python-pbr python-pyasn1 python-requests
  python-rfc3339 python-tz python-urllib3
Suggested packages:
  python-acme-doc python-cryptography-doc python-cryptography-vectors python-enum34-doc python-funcsigs-doc python-mock-doc python-openssl-doc python-openssl-dbg doc-base python-socks python-ntlm
The following NEW packages will be installed:
  python-acme python-cffi-backend python-cryptography python-dnspython python-enum34 python-funcsigs python-idna python-ipaddress python-mock python-ndg-httpsclient python-openssl python-pbr python-pyasn1
  python-requests python-rfc3339 python-tz python-urllib3
0 upgraded, 17 newly installed, 0 to remove and 68 not upgraded.
Need to get 0 B/917 kB of archives.
After this operation, 5,228 kB of additional disk space will be used.
Do you want to continue? [Y/n] y
Selecting previously unselected package python-cffi-backend.
(Reading database ... 47280 files and directories currently installed.)
Preparing to unpack .../python-cffi-backend_1.4.2-2~bpo8+1_i386.deb ...
Unpacking python-cffi-backend (1.4.2-2~bpo8+1) ...
Selecting previously unselected package python-enum34.
Preparing to unpack .../python-enum34_1.0.3-1_all.deb ...
Unpacking python-enum34 (1.0.3-1) ...
Selecting previously unselected package python-idna.
Preparing to unpack .../python-idna_2.0-3~bpo8+1_all.deb ...
Unpacking python-idna (2.0-3~bpo8+1) ...
Selecting previously unselected package python-ipaddress.
Preparing to unpack .../python-ipaddress_1.0.16-1~bpo8+1_all.deb ...
Unpacking python-ipaddress (1.0.16-1~bpo8+1) ...
Selecting previously unselected package python-pyasn1.
Preparing to unpack .../python-pyasn1_0.1.9-1~bpo8+1_all.deb ...
Unpacking python-pyasn1 (0.1.9-1~bpo8+1) ...
Selecting previously unselected package python-cryptography.
Preparing to unpack .../python-cryptography_1.3.4-1~bpo8+2_i386.deb ...
Unpacking python-cryptography (1.3.4-1~bpo8+2) ...
Selecting previously unselected package python-dnspython.
Preparing to unpack .../python-dnspython_1.15.0-1~bpo8+1_all.deb ...
Unpacking python-dnspython (1.15.0-1~bpo8+1) ...
Selecting previously unselected package python-funcsigs.
Preparing to unpack .../python-funcsigs_1.0.2-3~bpo8+1_all.deb ...
Unpacking python-funcsigs (1.0.2-3~bpo8+1) ...
Selecting previously unselected package python-openssl.
Preparing to unpack .../python-openssl_16.0.0-1~bpo8+1_all.deb ...
Unpacking python-openssl (16.0.0-1~bpo8+1) ...
Selecting previously unselected package python-ndg-httpsclient.
Preparing to unpack .../python-ndg-httpsclient_0.4.2-1~bpo8+1_all.deb ...
Unpacking python-ndg-httpsclient (0.4.2-1~bpo8+1) ...
Selecting previously unselected package python-pbr.
Preparing to unpack .../python-pbr_1.8.0-4.1~bpo8+1_all.deb ...
Unpacking python-pbr (1.8.0-4.1~bpo8+1) ...
Selecting previously unselected package python-urllib3.
Preparing to unpack .../python-urllib3_1.16-1~bpo8+1_all.deb ...
Unpacking python-urllib3 (1.16-1~bpo8+1) ...
Selecting previously unselected package python-requests.
Preparing to unpack .../python-requests_2.11.1-1~bpo8+1_all.deb ...
Unpacking python-requests (2.11.1-1~bpo8+1) ...
Selecting previously unselected package python-tz.
Preparing to unpack .../python-tz_2012c+dfsg-0.1_all.deb ...
Unpacking python-tz (2012c+dfsg-0.1) ...
Selecting previously unselected package python-rfc3339.
Preparing to unpack .../python-rfc3339_1.0-4~bpo8+1_all.deb ...
Unpacking python-rfc3339 (1.0-4~bpo8+1) ...
Selecting previously unselected package python-mock.
Preparing to unpack .../python-mock_2.0.0-3~bpo8+1_all.deb ...
Unpacking python-mock (2.0.0-3~bpo8+1) ...
Selecting previously unselected package python-acme.
Preparing to unpack .../python-acme_0.10.2-1~bpo8+1_all.deb ...
Unpacking python-acme (0.10.2-1~bpo8+1) ...
Processing triggers for man-db (2.7.0.2-5) ...
/usr/bin/mandb: can't open /usr/local/man/man1/duplicity.1: Permission denied
Setting up python-cffi-backend (1.4.2-2~bpo8+1) ...
Setting up python-enum34 (1.0.3-1) ...
Setting up python-idna (2.0-3~bpo8+1) ...
Setting up python-ipaddress (1.0.16-1~bpo8+1) ...
Setting up python-pyasn1 (0.1.9-1~bpo8+1) ...
Setting up python-cryptography (1.3.4-1~bpo8+2) ...
Setting up python-dnspython (1.15.0-1~bpo8+1) ...
Setting up python-funcsigs (1.0.2-3~bpo8+1) ...
Setting up python-openssl (16.0.0-1~bpo8+1) ...
Setting up python-ndg-httpsclient (0.4.2-1~bpo8+1) ...
Setting up python-pbr (1.8.0-4.1~bpo8+1) ...
update-alternatives: using /usr/bin/python2-pbr to provide /usr/bin/pbr (pbr) in auto mode
Setting up python-urllib3 (1.16-1~bpo8+1) ...
Setting up python-requests (2.11.1-1~bpo8+1) ...
Setting up python-tz (2012c+dfsg-0.1) ...
Setting up python-rfc3339 (1.0-4~bpo8+1) ...
Setting up python-mock (2.0.0-3~bpo8+1) ...
Setting up python-acme (0.10.2-1~bpo8+1) ...

At which point, python-acme 0.10.2-1 is installed, yet python-cerbot still fails:

$ sudo apt-get -t jessie-backports install python-certbot
Reading package lists... Done
Building dependency tree       
Reading state information... Done
Some packages could not be installed. This may mean that you have
requested an impossible situation or if you are using the unstable
distribution that some required packages have not yet been created
or been moved out of Incoming.
The following information may help to resolve the situation:

The following packages have unmet dependencies:
 python-certbot : Depends: python-acme (>= 0.9.3) but it is not going to be installed
E: Unable to correct problems, you have held broken packages.

Considering that sudo apt-get -t jessie-backports install certbot is the prominently specified installation method on certbot.eff.org, it’d be worth finding out why this is occurring. Thanks!

-Nikhil