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Several people have reported that in PuTTY's implementation of the Windows jump list, when a session is "pinned" to the taskbar, it does not disappear from the "Recent Sessions" section (so it appears in two places).
We've reproduced this, and it's not ideal. Unfortunately it doesn't seem to be under our control -- this part of the "jump list" feature is managed by Windows. Microsoft's documentation says:
The user might decide to pin one or more of the destinations provided in the custom category to the Jump List. The list of pinned destinations is not available to the application, but duplication is prevented by the UI so no extra action is required of the application. Visually, a pinned item moves to the Pinned section of the Jump List and disappears from its original location.
But Windows seems to be failing to do this here.
This aberrant behaviour is not apparent with other applications using Jump Lists, such as Notepad and Internet Explorer. Not sure what the significant difference is. The other apps are using the standard Recent/Frequent categories, whereas PuTTY has a custom "Recent Session" category.