It's updating fine from what I see. Both https://gerrit.wikimedia.org/r/#/admin/projects/wikimedia/TransparencyReport-private and the repo on the server are at
commit 12f441fca87ea5ec590aef1befb10b40db5b7497 Author: Siddharth11 <firstname.lastname@example.org> Date: Wed Feb 21 11:17:38 2018 +0530 Add a new row in requests breakdown table Change-Id: If1b977a6ca7eeb61b1afd06a9fb81458afc9c4ac
so the update process works just fine. Not only that, but https://transparency.wikimedia.org/private/privacy.html does indeed show the extra added entry.
Yes, please separate task.
The reason was that puppet was disabled on the instance, so puppet didn't run and therefore didn't clone.
The reason it was disabled was that we had to once do a content revert for another microsite for research and then i forgot to re-enable it later when it was possible.
The fix was that he asked on IRC and joe saw it and re-enabled puppet runs again.
The "prevent it from happening" again part is that i will try to not forget it again and always set a reason when disabling puppet. ;)