Welcome to CMSMS, lmj!
My first recommendation would be that you use the Uploads module for this, rather than the built-in file manager. Uploads makes what you're doing extremely easy.
So, download and install the Uploads mod (find it through the Module Manager or here: dev.cmsmadesimple.org/project/files/9 , then upload your newsletters again via Uploads.
Have a read through the module Help, and post back if you have more questions!
How make clickable link to file in file manager
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