Your pictures and other files may not go through if the timestamp on the file/image message does not match what is being reported by your device.
To resolve, please try setting the time/date to automatically update on the device, then restart the device, open Wickr, and try sending attachments again:
Android:
https://www.androidcentral.com/why-wont-my-phone-keep-right-time (the "manual" version then the "forced" version if manual does not work.)
iOS:
https://support.apple.com/en-us/HT203483
Windows:
https://www.makeuseof.com/tag/3-reasons-windows-computer-loses-time-date/ (#2)
Mac:
http://osxdaily.com/2016/05/07/fix-mac-showing-wrong-time-date/
Ubuntu:
https://www.digitalocean.com/community/tutorials/how-to-set-up-time-synchronization-on-ubuntu-16-04
If your images/files are still not going through, please contact wickr-support@amazon.com and let us know!
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