A Complex Software Engineering Problem
First announced in May 2020, Microsoft’s efforts to deliver Outlook roaming signatures in the click-to-run version of Outlook desktop (part of Microsoft 365 apps for enterprise) have stalled several times since. The latest information in Microsoft 365 roadmap item 60371 points to preview in September 2022 and general availability in October 2022. Given Microsoft’s record with this feature so far, few would bet that they will achieve this date.
As I explained in my original May 2020 post, the current implementation of Outlook signatures in the desktop client makes them more difficult to manipulate than the OWA equivalent, which require a simple update using the Set-MailboxMessageConfiguration cmdlet.
You’d hope that Microsoft has come up with a simpler and more elegant implementation for Outlook roaming signatures, but that’s no reason why it is taking Microsoft so long to deliver a solution to a problem that many other companies have solved, especially with their access to internal structures of Exchange Online and Outlook. According to Microsoft 365 message center notification MC305463 (December 15, now unavailable in the message center), the delay is due to the need for “further stabilization.”
Cynics might note that Microsoft finishes its FY22 fiscal year on June 30, and engineering management will be keen to ship features before that milestone. We may yet see at least a public preview of Outlook roaming signatures soon.
Signature Settings in Mailboxes
The roadmap item promises that Outlook will store signature information in the cloud, likely meaning that Outlook will retrieve signatures from a hidden folder in the Non-IPM section of Exchange Online mailboxes. Users who choose not to store signatures in the cloud will continue using the system registry to store signatures. Outlook 2016 and Outlook 2019 perpetual license clients will also use the system registry.
There’s no indication that Microsoft will bring roaming signatures to Exchange on-premises servers. Then again, Microsoft has gone dumb about the future of Exchange Server recently, with no news about when the successor to Exchange 2019 will appear.
The ISV Approach
Although customers are exasperated at the lack of Microsoft’s progress in delivering roaming signatures, I’m sure that ISVs like Code Two Software, Exclaimer, and Crossware are happy to have had two extra years to hone their signature management software to compete with Outlook roaming signatures. In 2020, Microsoft said that third-party add-ins will have to disable the Outlook feature to continue to work. They also committed to deliver an API to allow add-ins to work with roaming signatures. No details of the API are yet available, but given Microsoft’s focus on the Graph, it’s likely it will be a Graph API. Whether the API appears at the same time as roaming signatures or afterwards is another question.
On another front, signature management ISVs are leveraging the Outlook Signatures add-in API to integrate their products with Outlook desktop. First announced at Ignite 2020 and subsequently followed by a set of product releases from ISVs, the Outlook API is different to the one promised by the developers of roaming signatures and leverages the Outlook add-in model developed by the Office extensibility team. It’s a classic example of two solutions for the same problem coming from different Microsoft development groups.
I don’t think that Microsoft’s implementation of roaming signatures will materially affect ISV signature management products. After many years of development, these products are very sophisticated and tailored to meet the needs of enterprises who want common signatures used by all employees. Those who want an out of the box solution can have it today without waiting for roaming signatures by implementing signatures through transport rules. This approach works, it’s free, but it’s crude in comparison to what’s available in ISV products.
Confusing Outlook Signatures
As things stand, multiple different signature mechanisms exist for Outlook clients (OWA, Outlook for Windows, Outlook for Mac, Outlook mobile). This situation is due to the historical differences in client architectures and is confusing and cumbersome. Perhaps roaming signatures will be the first step on the road to a common signature used across all clients. Delivering such a capability might justify some of the two-year delay, but don’t hold your breath.
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