Looks like HAProxy's 'hard-stop-after'[1] config might be the solution
to this.

"""
Defines the maximum time allowed to perform a clean soft-stop.

This may be used to ensure that the instance will quit even if connections
remain opened during a soft-stop (for example with long timeouts for a proxy
in tcp mode). It applies both in TCP and HTTP mode.
"""

[1]http://cbonte.github.io/haproxy-dconv/1.8/configuration.html#3.1
-hard-stop-after

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https://bugs.launchpad.net/bugs/1828496

Title:
  service haproxy reload sometimes fails to pick up new TLS certificates

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