shortysks407
Since the "oldest" Express cannot connect, we may be able to assume that it is a 2.4-only device. (single band device). The other device now having issues, model 3930 is definitely a single-band device.
Only the model 3960 Roku Express is dual band. (capable of either 2.4ghz or 5 ghz connection).
For these 2.4 ghz Express models, you will need to make sure that the 2.4ghz band is enabled/on, and that its "wireless mode" is configured to use b/g/n (all three speed protocols) from within your router wireless settings.
The above wireless mode setting is necessary if you have a cable ISP (Xfinity/Comcast, AT&T, Cox, or Spectrum).
Xfinity/Comcast has recently issued another firmware update to some of its leased routers, and Spectrum is reportedly notorious for disabling its customers' 2.4ghz without notice.
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However, since the 14.40 error is usually more of a password issue, I would also make sure that your wifi password does not include special characters. Change it to just numbers and letters and see if you can connect. (ie. abcd1234).
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It is likely that either...
1. the 2.4ghz band is disabled/off
2. the 2.4ghz band wireless mode has been changed away from b/g/n
3. the wifi password contains special characters and is now having issues authenticating.
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If you are able to connect these Express devices to a mobile hotspot (if available), then confirms it is just an issue in the network settings/router.
Feel free to post back with router model number and name of your ISP if you are still having issues after changing the above settings.