(Please note that selected "component" might be completely wrong.)

I am using an automated upgrade based on Ansible, where it first downloads the specific Jenkins core debian package; and I am upgrading to an estimated > 95% of the weekly release versions of Jenkins 2 within 1-5 days after their release.

This was running without problem from about December 2016 (Jenkins v2.35) until today: Jenkins v2.134, that is for almost exactly 100 versions (interesting coincidence)...

Today it failed (at least 5 times in a row within ~30 minutes) like this:

PLAY [all] ********************************************************************GATHERING FACTS ***************************************************************ok: [jenkins2.ACME.com]TASK: [jenkins | install | Download specific jenkins version] *****************
failed: [jenkins2.ACME.com] => {"dest": "/tmp/jenkins-2.134.deb", "failed": true, "response": "Request failed: <urlopen error timed out>", "state": "absent", "status_code": -1, "url": "http://pkg.jenkins.io/debian/binary//jenkins_2.134_all.deb"}
msg: Request failedFATAL: all hosts have already failed -- abortingPLAY RECAP ********************************************************************
           to retry, use: --limit @/home/USER/jenkins-install.retryjenkins2.ACME.com        : ok=1    changed=0    unreachable=0    failed=1

My "solution" (or rather workaround?) was to set a timeout for Ansible "get_url" task (instead of default timeout of 10s), i.e. the line with "timeout: 20" is new:

# tasks file for installing jenkins
- name: install | Download specific jenkins version
 get_url:
 url: "{{ jenkins_pkg_url }}/jenkins_{{ jenkins_version }}_all.deb"
 timeout: 20
 dest: "/tmp/jenkins-{{ jenkins_version }}.deb"
 when: jenkins_version is defined and jenkins_version != ''

Please note that a manual download from https://pkg.jenkins.io/debian/ was also rather slowly starting and showing this target URL:

... but is NOW (~30 min later) starting fast again => so maybe the cloud is the "cause of and solution to all problems" (adapted quote of Homer Simpson)?