Hey everyone! We've been using CodeTwo Signatures software with the Send Items Update feature in our hybrid Exchange setup, where most mailboxes are in the cloud. Recently, I've noticed that signatures aren't refreshing in the Sent Items folder in the Outlook desktop app, although they work fine in Outlook Web App (OWA). I've checked the vendor FAQ and found that disabling cached mode in Outlook fixes the issue, but it was functioning properly with cached mode enabled for about two years. The recent changes we made include migrating from Exchange 2016 to the new SE, creating a new Federation Certificate, and a new OAuth certificate. I'm wondering if there's anything else we can check. Honestly, we'd prefer not to turn off cached mode for the entire organization. Any insights or tips would be greatly appreciated! Thanks!
2 Answers
Have you tried turning off caching, deleting the OST file, and then re-enabling caching? If the Send Items Update is working in the cloud, then it sounds like the issue is likely with the caching in Outlook. Sometimes, antivirus programs can interfere with the OST files too—just a thought. Also, check if your user's OST files have reached the size limit (50GB), as that could cause problems. It’d be helpful to know if new users are facing the same issues, or if any new add-ins were installed recently as well.
If you haven't done so already, it might be a good idea to create a support ticket directly with CodeTwo. Their customer support is usually pretty responsive. Just a heads up though, they might close the ticket quickly if they think it’s a common FAQ issue. But reaching out could lead to a better resolution!

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