diff --git a/ansible/files/gotrue.service.j2 b/ansible/files/gotrue.service.j2
index 2478e99e6..144448cc6 100644
--- a/ansible/files/gotrue.service.j2
+++ b/ansible/files/gotrue.service.j2
@@ -1,14 +1,56 @@
 [Unit]
 Description=Gotrue
 
+# Avoid starting gotrue while cloud-init is running. It makes a lot of changes
+# and I would like to rule out side effects of it running concurrently along
+# side services.
+After=cloud-init.service
+Wants=cloud-init.target
+
+# Given the fact that auth uses SO_REUSEADDR, I want to rule out capabilities
+# being modified between restarts early in boot. This plugs up the scenario that
+# EADDRINUSE errors originate from a previous gotrue process starting without
+# the SO_REUSEADDR flag (due to lacking capability at that point in boot proc)
+# so when the next gotrue starts it can't re-use a slow releasing socket.
+After=apparmor.service
+
+# We want sysctl's to be applied
+After=systemd-sysctl.service
+
+# UFW Is modified by cloud init, but started non-blocking, so configuration
+# could be in-flight while gotrue is starting. I want to ensure future rules
+# that are relied on for security posture are applied before gotrue runs.
+After=ufw.service
+
+# We need networking & resolution, auth uses the Go DNS resolver (not libc)
+# so it's possible `localhost` resolution could be unstable early in startup. We
+# care about this because SO_REUSEADDR eligibility checks the tuple
+# (proto, family, addr, port) meaning the AF_INET (ipv4, ipv6) could affect the
+# binding resulting in a second way for EADDRINUSE errors to surface.
+#
+# Note: We should consider removing localhost usage given `localhost` resolution
+# can often be racey early in boot, can be difficult to debug and offers no real
+# advantage in our infra. At the very least avoiding DNS resolved binding would
+# be a good idea.
+Wants=network-online.target systemd-resolved.service
+After=network-online.target systemd-resolved.service
+
+# Auth server can't start unless postgres is online, lets remove a lot of auth
+# server noise during slow starts by requiring it.
+Wants=postgresql.service
+After=postgresql.service
+
+# Lower start limit ival and burst to prevent the noisy flapping
+StartLimitIntervalSec=10
+StartLimitBurst=5
+
 [Service]
-Type=simple
+Type=exec
 WorkingDirectory=/opt/gotrue
-{% if qemu_mode is defined and qemu_mode %}
-ExecStart=/opt/gotrue/gotrue
-{% else %}
+
+# Both v2 & v3 need a config-dir for reloading support.
 ExecStart=/opt/gotrue/gotrue --config-dir /etc/auth.d
-{% endif %}
+ExecReload=/bin/kill -10 $MAINPID
 
 User=gotrue
 Restart=always
@@ -17,11 +59,36 @@ RestartSec=3
 MemoryAccounting=true
 MemoryMax=50%
 
+# These are the historical location of env files. The /etc/auth.d dir will
+# override them when present.
 EnvironmentFile=-/etc/gotrue.generated.env
 EnvironmentFile=/etc/gotrue.env
 EnvironmentFile=-/etc/gotrue.overrides.env
 
+# Both v2 & v3 support reloading via signals, on linux this is SIGUSR1.
+Environment=GOTRUE_RELOADING_SIGNAL_ENABLED=true
+Environment=GOTRUE_RELOADING_SIGNAL_NUMBER=10
+
+# Both v2 & v3 disable the poller. While gotrue sets it to off by default we
+# defensively set it to false here.
+Environment=GOTRUE_RELOADING_POLLER_ENABLED=false
+
+# Determines how much idle time must pass before triggering a reload. This
+# ensures only 1 reload operation occurs during a burst of config updates.
+Environment=GOTRUE_RELOADING_GRACE_PERIOD_INTERVAL=2s
+
+{% if qemu_mode is defined and qemu_mode %}
+# v3 does not use filesystem notifications for config reloads.
+Environment=GOTRUE_RELOADING_NOTIFY_ENABLED=false
+{% else %}
+# v2 currently relies on notify support, so we will enable it until both v2 / v3
+# have migrated to strictly use signals across all projects. The default is true
+# in gotrue but we will set it defensively here.
+Environment=GOTRUE_RELOADING_NOTIFY_ENABLED=true
+{% endif %}
+
 Slice=services.slice
 
 [Install]
 WantedBy=multi-user.target
+
diff --git a/testinfra/test_ami_nix.py b/testinfra/test_ami_nix.py
index 2325ff3d7..42442de18 100644
--- a/testinfra/test_ami_nix.py
+++ b/testinfra/test_ami_nix.py
@@ -374,12 +374,18 @@ def is_healthy(ssh) -> bool:
             try:
                 result = run_ssh_command(ssh, command)
                 if not result["succeeded"]:
-                    logger.warning(f"{service} not ready")
+                    info_text = ""
+                    info_command = f"sudo journalctl -b -u {service} -n 20 --no-pager"
+                    info_result = run_ssh_command(ssh, info_command)
+                    if info_result["succeeded"]:
+                        info_text = "\n" + info_result["stdout"].strip()
+
+                    logger.warning(f"{service} not ready{info_text}")
                     return False
+
             except Exception:
                 logger.warning(f"Connection failed during {service} check")
                 return False
-
         return True
 
     while True: