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edge 500 constantly needs updates

Greetings, I have an older but well functioning Edge 500 that wants me to do updates EVERY TIME I  plug it in. So I do them, disconnect the unit (properly) plug it back in and there it is again not 30 seconds after doing the update. Could somebody please tell me what the issue might be? In case it matters, there are times when the unit disconnects from the computer without being physically disconnected and is then not recognized by the computer until it is physically disconnected an then reconnected. There has been a recent message telling me that there was a problem with the drive and that a "scan and fix" was recommended. This was done and no issues were found.

Also when I sign into Garmin express with UN and PSWD it immediately wants me to sign in again. I ignore this, turn that dialogue box off and I am into the site, Why is this happening. I am on a new computer with windows 10 and I never had issues like this with my old windows 7 machine. In the past I never saw the Garmin express connection, it just happened and I was able to go directly to Garmin connect and view my rides when the sync was complete and the message flashed across the screen.

Is there a problem with compatibility? Is my unit not accepting the updates or is the site having issues? Is my unit failing? Looking for potential answers to these issues as it is becoming quite annoying.

Thanks for any assistance that you may offer.