Audio will not be routed to the headphones at all if the machine boots with the headphones plugged in

Whenever I boot up my laptop with headphones already plugged in via the headphone jack, and attempt to play audio, no audio will play, even though the volume is up. I have to unplug my headphones and plug it back in for the audio to play to my headphones.

Steps to Reproduce:
1. With the machine powered off, plug in headphones into the audio jack
2. Power on the machine and log in
3. Open Audacity, or (in my case), open up a YouTube video and turn up the sound
4. Notice no audio plays

Expected Results:
Audio plays through the headphones without issue

Actual Results:
No audio plays at all.

This bug is present in 18.04.4, 19.10, AND the current beta of 20.04

Description: Ubuntu 18.04.4 LTS
Release: 18.04

pulseaudio:
  Installed: 1:11.1-1ubuntu7.4
  Candidate: 1:11.1-1ubuntu7.4
  Version table:
 *** 1:11.1-1ubuntu7.4 500
        500 http://us.archive.ubuntu.com/ubuntu bionic-updates/main amd64 Packages
        100 /var/lib/dpkg/status
     1:11.1-1ubuntu7 500
        500 http://us.archive.ubuntu.com/ubuntu bionic/main amd64 Packages

ProblemType: Bug
DistroRelease: Ubuntu 18.04
Package: pulseaudio 1:11.1-1ubuntu7.4
ProcVersionSignature: Ubuntu 5.3.0-45.37~18.04.1-generic 5.3.18
Uname: Linux 5.3.0-45-generic x86_64
ApportVersion: 2.20.9-0ubuntu7.14
Architecture: amd64
AudioDevicesInUse:
 USER PID ACCESS COMMAND
 /dev/snd/controlC0: gdm 1181 F.... pulseaudio
                      seija 1504 F.... pulseaudio
 /dev/snd/pcmC0D0p: seija 1504 F...m pulseaudio
Date: Sun Apr 5 13:01:13 2020
InstallationDate: Installed on 2020-04-04 (1 days ago)
InstallationMedia: Ubuntu 18.04.4 LTS "Bionic Beaver" - Release amd64 (20200203.1)
ProcEnviron:
 TERM=xterm-256color
 PATH=(custom, no user)
 LANG=en_US.UTF-8
 SHELL=/bin/bash
PulseList:
 Error: command ['pacmd', 'list'] failed with exit code 1: Home directory not accessible: Permission denied
 No PulseAudio daemon running, or not running as session daemon.
SourcePackage: pulseaudio
Symptom: audio
UpgradeStatus: No upgrade log present (probably fresh install)
dmi.bios.date: 05/15/2019
dmi.bios.vendor: Dell Inc.
dmi.bios.version: 1.2.3
dmi.board.name: 09YTN7
dmi.board.vendor: Dell Inc.
dmi.board.version: A00
dmi.chassis.type: 10
dmi.chassis.vendor: Dell Inc.
dmi.modalias: dmi:bvnDellInc.:bvr1.2.3:bd05/15/2019:svnDellInc.:pnInspiron5570:pvr:rvnDellInc.:rn09YTN7:rvrA00:cvnDellInc.:ct10:cvr:
dmi.product.family: Inspiron
dmi.product.name: Inspiron 5570
dmi.product.sku: 0810
dmi.sys.vendor: Dell Inc.