Using classic Outlook for Windows in business environments
Hi Darlene,
After conducting some testing on my end (Classic Outlook Version 2609, Build 20430.20092), I was able to locate OneDrive under More Apps, and then right-click the icon and select Pin to keep it visible.
Based on this behavior, OneDrive appears to be surfaced as an Outlook app that can be pinned from the navigation area rather than as a traditional COM add-in.
If you haven't already, you may want to try this approach and see whether it allows the OneDrive icon to remain pinned between sign-ins. If the OneDrive icon disappears again after being pinned, you may want to contact your IT administrator for further assistance. They can check whether the behavior is specific to your account and, if necessary, open a support case with Microsoft for further investigation.
I hope this information is helpful.