Thanks, I don't see anything special in the journal. Would be worth
testing under GNOME. It does sounds similar to bug #1858092 but you have
the SRU from that fix already...

** Changed in: network-manager-pptp (Ubuntu)
   Importance: Undecided => Low

** Changed in: network-manager-pptp (Ubuntu)
       Status: Incomplete => New

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https://bugs.launchpad.net/bugs/1873399

Title:
  VPN connections asking password every time

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