Troubleshooting Playbooks

Step-by-step diagnosis for the problems that arrive most: printers, VPN, Wi-Fi, Outlook, performance.

AD CS / Internal PKI Issues

Troubleshoot AD CS internal PKI issues — enrollment and template failures, CRL revocation-check errors, and certificate expiry cascades before reissuing.

AD Replication Issues

Fix Active Directory replication failures using repadmin — GPO version mismatches, password changes not propagating, and event IDs 1311/1388/1988.

Adobe Creative Cloud Licensing

Fix Adobe Creative Cloud sign-in loops, access-denied errors, and Admin Console entitlement gaps between named-user and shared-device licensing.

AutoCAD / Revit Issues

Troubleshoot Autodesk AutoCAD and Revit — FlexNet network license checkout failures, drawing corruption, and BIM central-model worksharing sync.

Backup Restore Request

Intake backup restore requests — deleted files, prior versions, mailboxes, servers — pinning down what, when, RPO limits, and verifying with requester.

Browser Issues

Diagnose browser problems — one broken site, SSO loops, crashes, extension conflicts — using profile isolation and extension bisect, not clear-everything.

BSOD Analysis

Triage Windows blue screens by stop code and faulting module, correlating recent patches, drivers, or hardware to split driver, storage, and RAM causes.

Citrix Basics

First-line playbook for Citrix Virtual Apps and Desktops (CVAD/DaaS) — VDA registration, StoreFront vs Workspace, hung sessions — before escalating.

DFS Namespace and Replication

Fix DFS-N referral failures and DFS-R replication backlog, conflicts, and staging-quota issues using health reports and backlog counts, not blind reinit.

DHCP Server Issues

Diagnose DHCP problems — APIPA 169.254 addresses, wrong-subnet leases, scope exhaustion, stuck failover pairs, and rogue DHCP servers on the LAN.

DMARC / SPF / DKIM Setup

Diagnose email authentication failures and build correct SPF, DKIM, and DMARC DNS records — new sending sources, alignment, and propagation expectations.

DNS & Domain Issues

Diagnose DNS resolution and domain-expiry problems by laddering client to resolver to authoritative — stale records, intranet failing, whole domain dark.

Entra Connect Sync Errors

Fix Entra Connect (Azure AD Connect) sync errors — export failures, duplicate attributes, quarantined objects, users missing in the cloud — no blind runs.

Exchange Hybrid Issues

Troubleshoot Exchange hybrid — mail stuck on-prem/cloud, blank free-busy, stalled migrations, user-not-found after moves — starting from mailbox ownership.

Exchange On-Prem Mail Flow

Diagnose on-prem Exchange transport — stuck queues, send/receive connector faults, TLS/cert failures, backpressure — using Queue Viewer and protocol logs.

Fax & eFax

Work fax tickets — dead analog lines, ATA fax page corruption, eFax cloud portals not sending or receiving — across the line, ATA, and portal matrix.

File Share Permissions

Diagnose access-denied file share tickets by laddering effective permissions across share vs NTFS vs inheritance and group membership, at least privilege.

Group Policy Troubleshooting

Diagnose GPO not applying — missing drive mappings, lock screens, software installs — by reading gpresult and walking scope, filtering, and inheritance.

Hardware Diagnostics

Work desktop and laptop hardware faults — no-boot, random shutdowns, disk noises, battery and thermal — through POST stages, SMART, and warranty routing.

Hyper-V Clustering

Troubleshoot Hyper-V failover clusters — quorum loss, CSV redirected or offline, failed live migrations, stuck node drains — from cluster and event logs.

IIS Web App

Diagnose IIS web app failures — app pool crashes, rapid-fail protection, binding and SSL problems, HTTP 500/502/503 codes — using HTTP.sys and FREB logs.

Internal DNS Server Issues

Fix AD-integrated internal DNS — stale records, external dead while internal works (or reverse), records vanishing — distinct from public DNS/domain.

Label and Receipt Printers

Troubleshoot Zebra thermal label and ESC/POS receipt printers — ZPL/EPL print language, driver mode, spooler, and network faults — distinct from MFPs.

LOB Application Framework

Generic playbook for any line-of-business app failure — dental, legal, accounting, ERP — identify vendor and version, pull logs, build escalation packets.

LOB Database Locks

Clear record-locked-by-another-user tickets in LOB apps — find the locking session in the vendor admin console and release it approved-only, never kill DB.

M365 Sign-in Issues

Diagnose Microsoft 365 and Entra sign-in failures — blocked sign-ins, MFA loops, repeated password prompts, device-trust errors — from the sign-in log.

Mac Support

The Windows tech's ladder for Mac tickets — keychain prompts, MDM enrollment, TCC app permissions, FileVault — mapping macOS causes vs Windows reflexes.

Mail Flow & Delivery

Diagnose email delivery — NDR bounces, mail not arriving, stuck outbound, one sender blocked — by decoding the bounce and tracing the actual mail path.

Mobile Device & MDM

Work mobile MDM tickets — enrollment failures, missing mail profiles, compliance blocks, lost/stolen device response — destructive actions need approval.

Mobile Email Setup

Set up corporate mail on a phone — new-device config, sync failures, MDM enrollment prompts, native Mail vs Outlook — holding the BYOD consent boundary.

NetSuite ERP

Support NetSuite ERP tickets as an MSP — roles and permissions, saved-search visibility, SuiteScript/REST/CSV integration errors — no financial edits.

Network Share Slowness

Diagnose slow SMB file shares — sluggish copies, crawling folder listings, one office fine — through SMB version, signing, AV filters, and DFS referrals.

Office Activation & Licensing

Fix Office / Microsoft 365 Apps activation — Product Deactivated, unlicensed mode, repeated prompts, shared-computer/RDS errors — detect the license type.

On-Prem to Cloud File Migration

Fix file-server to SharePoint Online and OneDrive migration issues: NTFS permission translation, path length, illegal characters, and sync errors.

OneDrive / SharePoint Sync

Diagnose OneDrive and SharePoint sync — stuck processing changes, missing files, red X icons — separating client state, library limits, and permissions.

OneDrive Known Folder Move

Work OneDrive Known Folder Move rollout tickets — missing Desktop, sync conflicts, path-length and invalid-character legacy files — without unhooking KFM.

Outlook Client Issues

Diagnose Outlook desktop crashes, hangs, broken search, password prompts, and crash-on-send using profile, data-file, and add-in isolation branches.

Outlook Search Issues

Fix Outlook search returning nothing or incomplete results by isolating local index vs server search and cached-mode window before rebuilding the index.

PaperCut / PrinterLogic

Diagnose PaperCut and PrinterLogic print-management issues: release stations, driver deployment failures, and quota/account problems from platform logs.

POS System Issues

Work POS tickets — frozen terminals, failed card payments, back-office sync — by splitting terminal, payment gateway, and back-office with a PCI boundary.

Printer Troubleshooting

Diagnose printing problems — nothing prints, stuck queues, garbled output, wrong printer, scan-to-email fails — via a spooler, driver, and network matrix.

QuickBooks Desktop Multi-User

Fix QuickBooks Desktop multi-user errors: H202/H505 hosting, -6000 series company file, stuck locks, via hosting mode and Database Server Manager checks.

QuickBooks Online Issues

Fix QuickBooks Online browser problems: bank-feed failures, multi-user role errors, cache and extension issues; distinguish QBO from Desktop before acting.

RADIUS / NPS Authentication

Diagnose 802.1X and RADIUS authentication failures on Windows NPS: Wi-Fi, wired, VPN rejects, certificates, and shared-secret issues via NPS event logs.

RD Gateway Issues

Fix Remote Desktop Gateway and RD Web Access problems: external RDP failures, certificate errors, CAP/RAP policy mismatches, and MFA integration failures.

RDS / AVD Troubleshooting

Diagnose Remote Desktop Services and Azure Virtual Desktop session issues: connect failures, profile hangs, licensing, black screens, missing printers.

Roaming Profiles & FSLogix

Fix FSLogix and roaming-profile failures on session hosts: cannot attach VHD, temp profiles, sign-in hangs, and settings loss via FSLogix log codes.

Sage 50 / Sage 100

Diagnose Sage 50 and Sage 100 problems: data-path faults, share permissions, Pervasive/Actian PSQL engine service, and multi-user access errors at close.

SCADA / OT Awareness

Support OT-adjacent tickets safely: hard IT vs SCADA/PLC/HMI/ICS boundary, never touching controllers, and routing to the correct OT or vendor owner.

Scanner & Copier Fleet

Fix MFP and copier scan-to-folder failures after SMB or credential changes, address-book cleanup, firmware quirks, and panel errors on leased fleets.

SharePoint On-Prem

Diagnose on-premises SharePoint Server: search crawl failures, stale results, content-database mounting, and permission inheritance via ULS crawl logs.

Slow Computer

Triage a slow-computer ticket via resource hogs, disk health, startup load, and profile weight, ending with reimage or replace decision criteria.

SQL Backup and Maintenance

Fix SQL Server backup issues: runaway log growth, FULL vs SIMPLE recovery model, missing log backups, VSS conflicts, and broken point-in-time recovery.

SQL Server Performance

Diagnose SQL Server slowness: blocking, deadlocks, missing indexes, stale statistics, tempdb contention, and parameter sniffing via live wait stats.

SSL Certificate Renewal

Handle SSL and TLS certificate renewals: browser warnings, service certificate expiry, issuer-specific renewal paths, and required service restarts.

SSL Inspection Issues

Diagnose TLS/SSL inspection breakage: pinned apps failing, firewall certificate warnings, apps broken only on corporate networks, and bypass routing.

Teams Call Quality

Fix Microsoft Teams call quality: choppy audio, robotic voice, frozen video, and drops via CQD-style device, machine, and network path layer isolation.

Teams Issues

Diagnose Microsoft Teams sign-in loops, meeting join failures, no audio or video, stuck presence, and guest access, with cache reset used sparingly.

Teams Rooms AV

Fix Microsoft Teams Rooms devices: room account sign-in, camera, mic, display, touch console health, calendar join failures, and restart discipline.

Ticket Research Copilot

Read-only research sweep for an in-progress ticket: similar resolved tickets, KB, IT Glue and Hudu docs, and live RMM device state as a cited brief.

Troubleshooting Ladder

Base skill defining the order every troubleshooting playbook works in — history, documentation, blast radius, versions, verbatim evidence, then branch — and how it closes out.

Veeam Restore Operations

Run Veeam restores end to end: pick file-level, application-item, full-VM, or Instant Recovery, choose the right point, target a safe location, verify.

Vendor Outage Checker

Check vendor status pages and outage reports for M365, ISPs, and SaaS apps, then post sourced findings to the ticket to confirm is it down for everyone.

VMware vSAN and vMotion

Diagnose VMware vSphere: vSAN health warnings, resync storms, vMotion and DRS migration failures, datastore latency, and APD or PDL via vCenter events.

VoIP Phone Matrix

Diagnose VoIP problems: inbound calls failing, ring group misbehavior, one-way audio, dead phones, provisioning fails, by splitting phone vs site vs trunk.

VPN Troubleshooting

Diagnose VPN issues: won't connect, authenticates then no traffic, drops while remote, or can't reach resources by name via a client and DNS matrix.

Wi-Fi & Network Troubleshooting

Diagnose Wi-Fi and LAN issues: slow or dropping Wi-Fi, connection failures, dead zones, and internet-down reports by laddering user to AP to site scope.

Windows 11 Migration Issues

Handle post-upgrade Windows 11 migration tickets: driver regressions, reset default apps, missing printers, moved features, with rollback window checked.

Windows Profile Corruption

Fix Windows profile corruption and temporary-profile logons: confirm via profile-service event IDs, choose repair vs rebuild, and preserve user data first.

Windows Update Client Failures

Diagnose Windows Update client failures: 0x8024xxxx and 0x800Fxxxx errors, update loops and rollbacks, and stuck scans across WU, WSUS, and Intune sources.

WSUS Patching Infrastructure

Diagnose WSUS server-side issues: clients not checking in, 0% downloads, console crashes, unapproved-but-never-arriving updates, and database bloat.