Could you provide a link to the hardware you are using? like 4go board
and ugreen usb 3.1 case?

And btw if you connect a normal usb flash drive, does this issue happen?

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https://bugs.launchpad.net/bugs/1857760

Title:
  Raspberry Pi 4 loose Wifi connection when connecting external SSD

Status in linux-raspi2 package in Ubuntu:
  New

Bug description:
  When I connect an external SSD (Samsung 850 EVO 500 Go in a UGREEN USB
  3.1 case) on my Raspberry Pi 4 (4Go) the Wifi stop working. It is easy
  to reproduce, either en USB3 or USB2 connectors.

  The SSD is mounted, only the Wifi fails.

  The problem does not occurs on a fresh Rasbian.

  The problem does not occurs if I connect the SSD case on my keyboard
  (a R.Pi keyboard including a USB hub). Only if I connect the SSD
  directly on the R.Pi.

  When I disconnect the SSD case, the Wifi generally gets back, but
  sometimes I had to set the wifi OFF then ON (through gnome gui
  tooling). I don't have to reboot.

  ProblemType: Bug
  DistroRelease: Ubuntu 19.10
  Package: linux-image-5.3.0-1014-raspi2 5.3.0-1014.16
  ProcVersionSignature: Ubuntu 5.3.0-1014.16-raspi2 5.3.10
  Uname: Linux 5.3.0-1014-raspi2 aarch64
  ApportVersion: 2.20.11-0ubuntu8.2
  Architecture: arm64
  CurrentDesktop: ubuntu:GNOME
  Date: Sat Dec 28 14:16:44 2019
  SourcePackage: linux-raspi2
  UpgradeStatus: No upgrade log present (probably fresh install)

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