re: “scale to fit”
Sounds to me like you’re using an old version of Connections. Older version of Connections, just like WordPress, did not rescale images that were uploaded before the size settings was changed. The only way to have the image rescaled is to reupload the image.
With that said … newer version of Connections will dynamically resize images to match the size in the settings or the size defined in the template (some commercial template require a specific size and will enforce it). If you need that feature, you’ll have to update Connections.
Hope that help!