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Hi and welcome to JustAnswer, I’m Louie. Sorry you had to wait awhile but I’ll do my best to help.Initially, how was the Kindle updated please?
Was this Kindle purchased from Amazon using your account?
Logging in into your Amazon account, does it show up among "Your Content and Devices" ?
After the factory reset and immediately after turning it on, was a password *****?
"...don't have passwords turned on..." for your WiFi / router?
Has it been like that with whispersync since then; i.e. "....device uses whispersync not wifi..."
Have you tried turning off Whispersync even if just for test purposes?
In the "Manage Your Content and Devices" page of your Amazon account?
Thank you for your patience.
Second to the last question please; what is the serial number of your Kindle?
Even if just to confirm the update was complete and correct, please click HERE.
Have you brought this to the attention of Amazon?
Based on all of the above, it would appear to be an internal hardware issue.
Good luck and thank you for the opportunity to exchange information.