Re: [Fed-Talk] Outlook 16.69 (23010700) attempts to encrypt all outgoing
Re: [Fed-Talk] Outlook 16.69 (23010700) attempts to encrypt all outgoing
- Subject: Re: [Fed-Talk] Outlook 16.69 (23010700) attempts to encrypt all outgoing
- From: "Blumenthal, Uri - 0553 - MITLL via Fed-talk" <email@hidden>
- Date: Mon, 30 Jan 2023 23:07:17 +0000
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- Thread-topic: [Fed-Talk] Outlook 16.69 (23010700) attempts to encrypt all outgoing
IMHO, “New Outlook” is totally broken, S/MIME-wise at least. So far, I’m
keeping “old Outlook” – but my IT is warning me that at some point it’s going
to become “new Outlook” only. At which point, probably, S/MIME will quit
working and we’ll be back to Apple Mail or Thunderbird (or MS Teams 😃).
TNX
--
V/R,
Uri
There are two ways to design a system. One is to make it so simple there are
obviously no deficiencies.
The other is to make it so complex there are no obvious deficiencies.
- C. A. R. Hoare
From: Jeff Haferman via Fed-talk <email@hidden>
Reply-To: Jeff Haferman <email@hidden>
Date: Monday, January 30, 2023 at 17:12
To: Fed Talk <email@hidden>
Subject: [Fed-Talk] Outlook 16.69 (23010700) attempts to encrypt all outgoing
Not sure how many of you are using Outlook 16.69 923010700), but since Jan 11,
it attempts to encrypt all outgoing emails (and fails).
Through trial-and-error, I was able to get things to "work" by toggling "New
Outlook" off. When "New Outlook" is toggled on, outgoing email bounces and I in
the bounce I see something that looks like:
Remote Server returned '550 5.6.0 M2MCVT.StorageError.Exception:
ConversionFailedException - <unknown>, Content conversion: Invalid S/MIME
encrypted message.; storage error in content conversion.'
Original message headers:
Authentication-Results: dkim=none (message not signed)
header.d=none;dmarc=none action=none header.from=nps.edu;
Received: from MN2PR13MB4511.namprd13.prod.outlook.com (2603:10b6:208:1b7::27)
by PH7PR13MB5575.namprd13.prod.outlook.com (2603:10b6:510:139::12) with
Microsoft SMTP Server (version=TLS1_2,
cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.5986.18; Wed, 11 Jan
2023 18:43:28 +0000
Received: from MN2PR13MB4511.namprd13.prod.outlook.com
([fe80::f9a9:2064:b6ba:f1c]) by MN2PR13MB4511.namprd13.prod.outlook.com
([fe80::f9a9:2064:b6ba:f1c%7]) with mapi id 15.20.5986.018; Wed, 11 Jan 2023
18:43:28 +0000
Content-Type: application/ms-tnef; name="winmail.dat"
Content-Transfer-Encoding: binary
Because my "work around" allows me to get things done, I just have kept the
"New Outlook" toggled off. I haven't been able to find anything about this
behavior via web search. I don't have many co-workers that are using Mac +
Outlook, so I'm just sucking it up. But now another co-worker is experiencing
the issue.
Just figured I'd report it here in case anyone has some ideas.
Jeff
Attachment:
smime.p7s
Description: S/MIME cryptographic signature
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