Yes! This has been happening to me as well. This workaround has worked reliably for me...
1. Stop any updates that are currently trying.
2. Turn off Wifi.
3. Find the smallest app that needs updating (to conserve OTA data) and tap Update.
4. Once it starts downloading, kick on Wifi.
5. Hit Update All. The apps should start downloading and installing.
Tried to stick a proxy between the phone and my computer to sniff the packets, but that failed... Not sure why this is happening. Same issue on my home and work wifi.
A reboot also fixes it... But that takes forever. 🙂
-T