HD-12 does not hold "Remember me"
After checking the "Remember me" each time via the web, I am faced with typing the same login information Am I doing something wrong?

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Question. Are you using the my.rain machine.com or directly through your internal network, using an IP and port 8080?
I have found that direct to the device, it does not work to remember you. But through my.rain machine.com it does.
I like using the direct approach as to they do not have to track, but I also find it a pain to not remember me. I have then mainly stuck with the my.rainmahine.com way until I figure out a way for it to remember on a direct connection.
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Sorry - the RainMachine itself does not hold certificates, to hard to keep them updated, etc. One reason why the company uses my.rainmachine.com - they have one common certificate that covers any *.rainmachine.com.
You maybe able to set an exception. I do not run Edge and not familiar with it, for these type of things. I will get to a machine that runs Edge and try to check it out.
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I think that your password is "remembered" using a cookie in your browser.
There may be a setting in Edge to remember cookies and even "for certain sites" since you don't want to necessarily remember ALL cookies.
I know Firefox on win 7 has that. Not really familiar with win 10 and Edge.
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