startup-it-troubleshooting – Other skill for AI agents

Startup IT Troubleshooting

Runbooks for startups and small teams where engineers double as the IT department.

When to Use

You are the "accidental IT person." Nobody has IT in their title, but laptops freeze, Wi-Fi drops during investor demos, someone gets locked out of Google Workspace at midnight, and a new hire starts Monday with zero accounts. Commands are platform/version-specific examples. Start read-only, preserve current configuration and apply only authorized, reviewed changes to the exact account/device.

Priority triage: (1) Company-wide outages, (2) Executive/customer-facing blockers, (3) Team-wide degradations, (4) Individual workstation issues. Always ask: "How many people are affected?" and "Is revenue impacted?"

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SSO / Identity Lockouts

Google Workspace via GAM

# Obtain GAM from its official project, pin/verify the release and inspect installation instructions before installing.
gam oauth create                                                     # authorize

# Reset through the approved secure admin workflow; never literal or generated passwords in process argv.
gam update user [email protected] suspended off       # unsuspend locked-out user
gam user [email protected] signout                    # force sign-out all sessions
gam user [email protected] update backupcodes         # new MFA backup codes
# Do not disable2SV as routine recovery; use verified recovery/backup methods.

Okta API

: "${OKTA_DOMAIN:?Set the authorized Okta domain}"
: "${OKTA_API_TOKEN:?Inject admin token securely}"
: "${OKTA_USER_ID:?Verify the exact target user}"
curl -X POST -H "Authorization: SSWS $OKTA_API_TOKEN" "https://$OKTA_DOMAIN/api/v1/users/$OKTA_USER_ID/lifecycle/unlock"
curl -X POST -H "Authorization: SSWS $OKTA_API_TOKEN" "https://$OKTA_DOMAIN/api/v1/users/$OKTA_USER_ID/lifecycle/reset_password?sendEmail=true"
curl -X POST -H "Authorization: SSWS $OKTA_API_TOKEN" "https://$OKTA_DOMAIN/api/v1/users/$OKTA_USER_ID/lifecycle/reset_factors"
curl -X DELETE -H "Authorization: SSWS $OKTA_API_TOKEN" "https://$OKTA_DOMAIN/api/v1/users/$OKTA_USER_ID/sessions"

MFA recovery flow: Verify identity with the established independent recovery procedure (a video call alone is insufficient), generate backup codes or reset factors, have user re-enroll immediately, confirm old device is deregistered, log the incident.

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Network resets, DNS overrides and VPN resets can break managed policy or remote access. Record current resolver/interface settings first, choose the actual interface and restore them after diagnostics. Public DNS may not resolve internal zones and may disclose internal queries. Package/update/reboot, encryption, account transfer and printer-queue changes below are separate mutating actions, not an automatic checklist.

Network Troubleshooting

Wi-Fi Debugging

# macOS
/System/Library/PrivateFrameworks/Apple80211.framework/Versions/Current/Resources/airport -I
networksetup -setairportpower en0 off && sleep 2 && networksetup -setairportpower en0 on
sudo dscacheutil -flushcache && sudo killall -HUP mDNSResponder

# Linux
nmcli device wifi list && nmcli connection show --active
nmcli device disconnect wlan0 && nmcli device connect wlan0
sudo systemd-resolve --flush-caches

netsh wlan show interfaces
netsh wlan disconnect; netsh wlan connect name="OfficeWiFi"
ipconfig /flushdns
netsh winsock reset  # full stack reset, reboot after

DNS Issues

nslookup company.com 8.8.8.8            # test against known-good DNS
dig @1.1.1.1 company.com                # Linux/macOS detail
sudo networksetup -setdnsservers Wi-Fi 8.8.8.8 8.8.4.4  # macOS temp override

$a = Get-NetAdapter | Where-Object {$_.Status -eq "Up"}
Set-DnsClientServerAddress -InterfaceIndex $a.ifIndex -ServerAddresses ("8.8.8.8","8.8.4.4")

VPN Not Connecting

nc -zv vpn.company.com 443                         # test port reachability
sudo wg show                                        # WireGuard status
sudo wg-quick down wg0 && sudo wg-quick up wg0     # restart WireGuard
tailscale status && sudo tailscale up --reset       # Tailscale re-auth

Slow Internet

speedtest-cli --simple        # bandwidth test (pip install speedtest-cli)
ping -c 50 8.8.8.8            # packet loss check
networkQuality -s              # macOS 12+ bufferbloat test

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Laptop Performance

Disk Space

df -h                                    # volume overview
du -sh ~/* | sort -rh | head -15         # biggest dirs in home
docker system df                         # Docker disk usage (common culprit)
docker system df -v                      # inventory; review exact unused artifacts/volumes before deletion
brew cleanup --prune=all                 # macOS Homebrew cleanup

Get-PSDrive -PSProvider FileSystem | Select Name,@{N='Free(GB)';E={[math]::Round($_.Free/1GB,2)}}
Get-ChildItem C:\ -Recurse -File -EA SilentlyContinue | Sort Length -Desc | Select -First 15 FullName,@{N='MB';E={[math]::Round($_.Length/1MB,2)}}

Memory Pressure and Runaway Processes

# macOS
memory_pressure
top -o rsize -l 1 -n 10 -stats pid,command,rsize
# Inspect exact processes and save work before quitting; avoid broad pkill patterns.

# Linux
free -h && ps aux --sort=-%mem | head -11
sudo dmesg | grep -i "oom\|out of memory"

Get-Process | Sort WorkingSet64 -Desc | Select -First 10 Name,@{N='MB';E={[math]::Round($_.WorkingSet64/1MB,2)}}
# Quit the verified application after saving work; force termination is a separate approved recovery.

Battery Health

system_profiler SPPowerDataType | grep -E "Cycle Count|Condition"  # macOS
upower -i /org/freedesktop/UPower/devices/battery_BAT0             # Linux

powercfg /batteryreport /output "$env:USERPROFILE\Desktop\battery.html"

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macOS Administration

profiles status -type enrollment          # MDM enrollment check
sudo systemsetup -getremotelogin          # inspect; enabling SSH changes remote access

# Homebrew fleet setup — standard Brewfile
cat > Brewfile <<'EOF'
brew "git"; brew "node"; brew "[email protected]"; brew "awscli"; brew "jq"; brew "gh"
cask "google-chrome"; cask "slack"; cask "1password"; cask "visual-studio-code"; cask "docker"; cask "zoom"
EOF
brew bundle install --file=Brewfile
brew bundle dump --file=~/Brewfile --force  # export current setup

# FileVault
sudo fdesetup status && sudo fdesetup enable  # store recovery key in 1Password

# Updates
softwareupdate -l  # schedule installation/restart only after approved downtime

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Windows Administration

gpresult /r; gpupdate /force             # check and refresh Group Policy

# Windows Update
Install-Module PSWindowsUpdate -Force -Scope CurrentUser
Get-WindowsUpdate  # review and schedule approved install/reboot
# If stuck: reset update components
Stop-Service wuauserv,cryptSvc,bits,msiserver -Force
# Follow the supported repair procedure; preserve diagnostics instead of blind recursive deletion.
Start-Service wuauserv,cryptSvc,bits,msiserver

# BitLocker
manage-bde -status C:
Enable-BitLocker -MountPoint "C:" -EncryptionMethod XtsAes256 -UsedSpaceOnly -TpmProtector

# Remote Desktop
Set-ItemProperty -Path 'HKLM:\System\CurrentControlSet\Control\Terminal Server' -Name "fDenyTSConnections" -Value 0
Enable-NetFirewallRule -DisplayGroup "Remote Desktop"

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Linux Desktop

# Ubuntu — fix broken packages
sudo apt --fix-broken install && sudo dpkg --configure -a && sudo apt update && sudo apt upgrade -y

# Fedora — fix broken packages
sudo dnf check && sudo dnf distro-sync && sudo dnf update -y

# Service failures
systemctl --failed
journalctl -p err -b

# Drivers
sudo ubuntu-drivers autoinstall                    # Ubuntu proprietary drivers
lspci | grep -i vga && sudo lshw -C display        # GPU info
sudo dmesg | grep -i firmware                       # missing firmware

# Display issues
xrandr --auto                                       # reset to auto-detect
xrandr --output HDMI-1 --mode 1920x1080 --rate 60  # force resolution
echo $XDG_SESSION_TYPE                              # Wayland vs X11 check

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Email / Calendar Issues

Google Workspace

gam user [email protected] show forwarding    # check rogue forwarding rules
gam user [email protected] delete forwarding  # remove forwarding
gam user [email protected] show delegates     # check email delegation
gam user [email protected] show filters       # check mail filters

Microsoft 365

Install-Module ExchangeOnlineManagement -Force -Scope CurrentUser
Connect-ExchangeOnline -UserPrincipalName [email protected]
Get-MessageTrace -SenderAddress [email protected] -StartDate (Get-Date).AddDays(-7) -EndDate (Get-Date)
Get-MailboxStatistics -Identity [email protected] | Select DisplayName,TotalItemSize

Email Deliverabili

… (full content is in the download package)