Istiaque: Feel free to take this if you have the time to look at it.

So it seems that the cron job to update the docs is actually commented out. The last update to the crontabs file for the git-processor user seems to have been made on 30th May, which correlates with the third-last git pull date.

Using git reflog --date=iso on the chrome src repo, some of the last entries are: 

cf0a94a HEAD@{2017-09-01 00:04:54 +0000}: pull: Fast-forward
a0a2b36 HEAD@{2017-08-26 05:48:09 +0000}: pull: Fast-forward
6dfa5a1 HEAD@{2017-05-30 22:12:11 +0000}: pull: Fast-forward
4523afe HEAD@{2017-05-30 21:23:28 +0000}: rebase finished: returning to refs/heads/master
4523afe HEAD@{2017-05-30 21:23:28 +0000}: checkout: moving from master to 4523afedd7271dcdd8a2d310e219ecb8c63fff63^0
9984205 HEAD@{2017-05-05 00:11:08 +0000}: pull: Fast-forward
f05a24a HEAD@{2017-05-04 23:56:31 +0000}: pull: Fast-forward
904fd51 HEAD@{2017-05-04 23:11:25 +0000}: pull: Fast-forward
7d2cbcf HEAD@{2017-05-04 22:56:57 +0000}: pull: Fast-forward
ac81f80 HEAD@{2017-05-04 22:09:12 +0000}: pull: Fast-forward
a038875 HEAD@{2017-05-04 21:56:31 +0000}: pull: Fast-forward

The 2 latest entries here were manual runs done by Istiaque, I believe. Hence it seems we somehow forgot to uncomment the cron job or maybe it was intended. Will wait for response and then uncomment the job if necessary. 

Aside: App engine also allows us to specify cron jobs. See https://cloud.google.com/appengine/docs/standard/python/config/cron. We should move over to that approach. That way all this can be version controlled and we won't need to SSH into a VM etc.

The following revision refers to this bug:
  https://chromium.googlesource.com/chromium/src.git/+/c95c9e17cf1f7f1107cd19d3db859dc307c1dd2f

commit c95c9e17cf1f7f1107cd19d3db859dc307c1dd2f
Author: Karan Bhatia <karandeepb@chromium.org>
Date: Mon Sep 11 19:05:47 2017

Extension Docserver: Increment version.

This CL updates the Docserver version. We will be migrating to a new VM instance
responsible for updating the Cloud datastore. Since the datastore entries are
versioned, this should ensure that any datastore updates do not affect the
currently served production version.

BUG= 760258 

Change-Id: I427ddb85fdb41c55db9afb63b5859c756afc3f02
Reviewed-on: https://chromium-review.googlesource.com/657922
Reviewed-by: Istiaque Ahmed <lazyboy@chromium.org>
Commit-Queue: Karan Bhatia <karandeepb@chromium.org>
Cr-Commit-Position: refs/heads/master@{#500991}
[modify] https://crrev.com/c95c9e17cf1f7f1107cd19d3db859dc307c1dd2f/chrome/common/extensions/docs/server2/app.yaml

Fixed. git pull was freezing probably because of the old git version (which couldn't be updated due to the VM running the outdated Debian 7). Migrating to a new VM seems to have fixed this for now.