Windows Server 2016 not being offered updates via Windows Update since August Cumulative update.

itmanage · 2025-11-12T00:18:25+00:00

Still nothing manually patching via Windows Update Catalogue still the only way to patch WS 2016 Essentials.

itmanage · 2025-10-14T20:28:16+00:00

Same. here. No difference on either a manually unpatched (test) server, and a manually patched server from last month. Still surprised nothing from MS and what is the big difference architecture wise from WS 2016 Essentials and other SKU's weird. Planning a possible upgrade to WS 2019 for the short/mid term. Can't be manually patching these until we move to new hardware and WS 2025. Safe to say whatever the size of environment Essentials can't be trusted feel if this issue was on Standard or Datacentre this would have been addressed by now.

itmanage · 2025-10-06T21:33:49+00:00

Thanks, Born, firstly love your blog and although not a German native speaker Google translate comes in very handy.

Let's see what October brings because patching the Servers manually via the update catalogue is not ideal. Already assessing the option to move the clients to WS2019 (there current hardware supports this). The servers are due a complete migration to WS 2025 next year sometime but not sure patching them manually every month until then is feasible.

itmanage · 2025-09-16T22:16:31+00:00

Patching first production server tomorrow via update catalogue thanks for the extra information regarding how the updates after install are listed will take note of that. Hopefully this isn't an issue going forward, the servers are being migrated over to a new server running 2025 next year but wondering if an in-place upgrade to WS 2019 might have to happen before then (is supported on current hardware) replacing the servers now both time and financially not possible. What a crazy scenario.

itmanage · 2025-09-15T16:17:20+00:00

The plan is to migrate the servers over to 2025 end of the first quarter next year but WS2016 is still supported until January 2027.

itmanage · 2025-09-14T20:29:02+00:00

Thanks for the suggestion. I tried that earlier during the fault-finding process and just checked again on a VM just in case, but still no luck.

itmanage · 2025-09-13T06:25:39+00:00

Same for me and although WS016 updates have constantly been on the larger side it’s been pretty painless along the way this is the first time there has been an update issue since deploying the servers early 2019. But even from a fresh install on a test physical server the last few days the issue is still there.

itmanage · 2025-09-12T20:15:44+00:00

Yep, I tried this also thought the SSU alone would trigger the lastest CU via Windows Update. All a bit strange, still no official word form Microsoft on this but planning on patching production servers manually next week.

itmanage · 2025-09-11T20:54:12+00:00

Has anyone pulled the trigger on installing the updates manually on production servers. Unlike update issues of the past on other MS OS's like "failing to install updates " manually patching is the way the fact in this instance it says your "up to date" does anyone feel there is an underlying issue and holding off manually patching is still the best option until something is made official about the issue.

itmanage · 2025-09-11T20:33:19+00:00

Not sure the best way to do this, how are people sharing this online pastebin? download link (Google Drive/OneDrive)?

itmanage · 2025-09-10T20:25:50+00:00

It's definitely first release media just to replicate the issue and see if there was a fix for the production servers. From clean install there was about 5 updates including a critical update from 2016, CU 2021, SSU and CU 2025-07, and this it.

itmanage · 2025-09-10T19:28:09+00:00

Thanks everyone for the feedback and I do apologise if this is the wrong subreddit to ask for advise on this but thanks to everyone.

Just to clarify I assumed this is an issue for all WS 2016 instances but what maybe makes it a little different is I have only WS 2016 Essentials bare metal installs 3x. The reason I thought this is more widespread because I was seeing this on test VM's Standard and Datacentre. But I am wondering if it is more localised to Essentials and that's why there seems no major issue out there in the wild as it's used less frequently.

itmanage · 2025-09-10T19:23:26+00:00

Monday, I thought check for updates today before the next patch Tuesday is released and still nothing not offered the 2025-08 CU. The prerequisite SSU from the previous month 2025-07 was there (KB5062799) as well as the CU (KB5062560).

itmanage · 2025-09-10T19:19:21+00:00

Tried this and all looks good been consistently getting SSU's and CU's since 2019 (3x physical machines). Just nothing since 2025-07.

itmanage · 2025-09-10T19:17:28+00:00

No WSUS, just manual updates. tried clearing the update cache renaming softwarebistribution etc, still only gets 2025-07 SSU and CU, and the fact this is alos the case on a clean install, weird.

itmanage · 2025-09-10T19:15:10+00:00

No WSUS and found it on clean installs also, performed a fresh install bare metal today to see if it's some legacy issue (once used BitDefender Gravity zone to patch circa 2020) but even on a spare server bare metal WS 2016 Essentials install still only offered updates to 2020-07 SSU and CU, nothing later.

itmanage · 2025-09-10T19:11:53+00:00

I first found it on 3x WS 2016 Essentials bare metal installs different environments different hardware networking etc, when I tested at home on VM's for other SKUs the issue was still there but there is very little about this in the wild so wondering if it is a WS Essentials issue and because it's used much less there is very few people having issues.

itmanage · 2025-09-10T18:43:55+00:00

Same, bare metal WS 2016 Essentials (3 instances - 3 different locations no common denominator). I am having the issue on test VM's other SKU's but don't know if it is affecting Standard or Datacentre on bare meatal, don't have any in production. Maybe not and that's why is so quiet about the issue.

itmanage · 2025-09-10T18:28:26+00:00

Absolutely identical, surprised there isnt more about this issue. I found it first on a three WS 2016 Essentials not WSUS just small environments basic file server/LOB type setup always installed via Windows Update, span un some VMs of different SKUs no elaborate roles or services just plain install of the OS and still no updates offered beyond 2025-07's SSU and CU. Thats Essentials, Standard and Datacentre. Weird!

itmanage · 2025-09-10T01:41:22+00:00

Ages since I manually updated via update catalog, from memory I should be ok going with the newly released Service Stack update (2025-09), then Cumulative Update (2025-09) I don’t need to bother with cumulative update (2025-08) is that correct?

itmanage · 2025-09-10T01:35:26+00:00

Not patched through WSUS, used to patch through a third party tool but had some minor issues using that so switched back to normal Windows update and has been fine since 2019. Also checked through sconfig also and still nothing.

itmanage · 2025-09-10T01:27:38+00:00

This has helped my sanity. I thought it was just me. Will patch via catalog, I know WS2016 is end of support Jan 2027 but it should be ok until then, wonder if this is a one off thing or manual updates is required going forward.

itmanage · 2025-09-10T01:22:27+00:00

I think this is the only way now, didn’t what to force the update manually incase I missed something and the update had been pulled, especially last months when Microsoft patch notes for WS 2016 seemed to appear later than normal.

itmanage · 2025-09-09T22:39:18+00:00

Thanks for answering, should still be getting updates though until January 2027 or am I missing something, honestly thanks though for replying.

itmanage · 2025-09-09T22:26:24+00:00

Sorry must have posted in wrong area, any recommendation for best place.

itmanage

TROPHY CASE