Noticed a similar issue today. With the difference that in my case,
sesman would never come up. Found out that I was hitting [1]. Had to use
workaround from [2].

Complete workaround was:

Fix was:

1. sudo bash -c 'export SYSTEMD_EDITOR="/usr/bin/vi" && systemctl edit
xrdp-sesman.service'

2. sudo systemctl edit xrdp-sesman

[Service]
Type=simple
ExecStartPre=/bin/sleep 20

Save the file.

3. sudo vi /etc/default/xrdp

SESMAN_OPTIONS="-n"

4. sudo systemctl stop xrdp-sesman xrdp

5. sudo systemctl start xrdp-sesman xrdp

[1] https://github.com/neutrinolabs/xrdp/issues/1652
[2] https://github.com/neutrinolabs/xrdp/issues/1652#issuecomment-675387354

** Bug watch added: github.com/neutrinolabs/xrdp/issues #1652
   https://github.com/neutrinolabs/xrdp/issues/1652

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https://bugs.launchpad.net/bugs/1766695

Title:
  xrdp-sesman fails to start at bootup

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