I am experiencing this same issue after upgrading from jessie to stretch

However these statements:

"Jul 27 20:18:21 hedwig isc-dhcp-server[17921]: Starting ISC DHCPv4 server:
dhcpddhcpd service already running (pid file /var/run/dhcpd.pid currenty
exists) ... failed!"

Especially:

"Hence, it seems the upgrade process leaves a dangling PID file around.
Removing that PID file manually solved the problem for me."

Is not quite true for me.  It it fails to start isc-dhcpd leave a dangling
file which must be removed manually before starting / restarting
isc-dhcpd.

it is 2019 does isc-dhcp server leave gangling /var/run/dhcpd.pid files on
failure to start?  The answer to this non rhetorical question... well
yes... for me it does. again... and again... and again.

--------------------------------

-- Unit isc-dhcp-server.service has begun starting up.
Mar 22 17:31:15 dungeon isc-dhcp-server[13036]: DHCPv4 interfaces are no
longer set by the INTERFACES variable in
Mar 22 17:31:15 dungeon isc-dhcp-server[13036]:
/etc/default/isc-dhcp-server.  Please use INTERFACESv4 instead.
Mar 22 17:31:15 dungeon isc-dhcp-server[13036]: Migrating automatically for
now, but this will go away in the future.
Mar 22 17:31:15 dungeon isc-dhcp-server[13036]: Launching IPv4 server only.
Mar 22 17:31:15 dungeon isc-dhcp-server[13036]: Starting ISC DHCPv4 server:
dhcpddhcpd service already running (pid file /var/run/dhcpd.pid currenty
exists) ... failed!
Mar 22 17:31:15 dungeon systemd[1]: isc-dhcp-server.service: Control
process exited, code=exited status=1
Mar 22 17:31:15 dungeon systemd[1]: Failed to start LSB: DHCP server.
-- Subject: Unit isc-dhcp-server.service has failed
-- Defined-By: systemd
-- Support: https://www.debian.org/support
--
-- Unit isc-dhcp-server.service has failed.
--
-- The result is failed.
Mar 22 17:31:15 dungeon systemd[1]: isc-dhcp-server.service: Unit entered
failed state.
Mar 22 17:31:15 dungeon systemd[1]: isc-dhcp-server.service: Failed with
result 'exit-code'.
Mar 22 17:33:02 dungeon systemd[1]: Starting LSB: DHCP server...
-- Subject: Unit isc-dhcp-server.service has begun start-up
-- Defined-By: systemd
-- Support: https://www.debian.org/support
--
-- Unit isc-dhcp-server.service has begun starting up.
Mar 22 17:33:02 dungeon isc-dhcp-server[13078]: Launching IPv4 server only.
Mar 22 17:33:02 dungeon isc-dhcp-server[13078]: Starting ISC DHCPv4 server:
dhcpddhcpd service already running (pid file /var/run/dhcpd.pid currenty
exists) ... failed!
Mar 22 17:33:02 dungeon systemd[1]: isc-dhcp-server.service: Control
process exited, code=exited status=1
Mar 22 17:33:02 dungeon systemd[1]: Failed to start LSB: DHCP server.
-- Subject: Unit isc-dhcp-server.service has failed
-- Defined-By: systemd
-- Support: https://www.debian.org/support
--
-- Unit isc-dhcp-server.service has failed.
--
-- The result is failed.
Mar 22 17:33:02 dungeon systemd[1]: isc-dhcp-server.service: Unit entered
failed state.
Mar 22 17:33:02 dungeon systemd[1]: isc-dhcp-server.service: Failed with
result 'exit-code'.
root@dungeon:/home/bit#
root@dungeon:/home/bit# rm /var/run/dhcpd.pid
root@dungeon:/home/bit# /etc/init.d/isc-dhcp-server restart
[ ok ] Restarting isc-dhcp-server (via systemctl): isc-dhcp-server.service.


Above is not first time... I experienced this at least up to three (3)
times while configuring.

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