On 22.01.2026 at 06:57 Gregory Rocher via mailop wrote:

> Le 21/01/2026 à 23:33, Andrew C Aitchison via mailop a écrit :
>> No idea whether it is related but Linux web-browsers tell me that the
>> certificate for download.microsoft.com is signed by an unknown issuer.
>> It is possible their issues are wider than just email.

> Hi
> On the download.microsoft.com certificate openssl sees a problem with the 
> chain yes
>> [grocher:~] $ date
>> jeudi 22 janvier 2026, 06:56:53 (UTC+0100) [grocher:~] $ openssl
>> s_client -connect download.microsoft.com:443
>> CONNECTED(00000003)
>> depth=0 C = US, ST = WA, L = Redmond, O = Microsoft Corporation, CN =
>> akamai.download.microsoft.com verify error:num=20:unable to get local
>> issuer certificate verify return:1
>> depth=0 C = US, ST = WA, L = Redmond, O = Microsoft Corporation, CN =
>> akamai.download.microsoft.com verify error:num=21:unable to verify the
>> first certificate verify return:1
>> depth=0 C = US, ST = WA, L = Redmond, O = Microsoft Corporation, CN =
>> akamai.download.microsoft.com verify return:1
>> ---
>> Certificate chain
>>  0 s:C = US, ST = WA, L = Redmond, O = Microsoft Corporation, CN = 
>> akamai.download.microsoft.com
>>    i:C = US, O = Microsoft Corporation, CN = Microsoft TLS G2 ECC CA OCSP 02
>> ---

Yeah, it's a bit messy. The endpoints behind download.microsoft.com return 
different certificates and the ones issued on 2026-01-13 are lacking the 
certificate chain. If your client is not already in possession of the 
intermediates "Microsoft TLS G2 ECC CA OCSP 02" and "Microsoft TLS ECC Root G2" 
the verification will fail.

But this is certainly unrelated to the SMTP errors. Guides from Al Iverson 
(https://www.spamresource.com/2020/08/help-im-blocked-at-microsoft-what-do-i.html)
 and Hetzner 
(https://docs.hetzner.com/robot/dedicated-server/troubleshooting/microsoft-blacklist/#olc-outlook-consumer)
 have been shared on this list in the past on how to solve that. In most cases 
it boils down to:
1. Open a ticket via the linked form
2. Wait
3. Escalate
4. Repeat steps 2. and 3. until the issue is solved

--
BR Oliver
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