My Essential IT Troubleshooting Guide

Simple Explanations for Real World Problems

One of my favorite seasons of my life. Serving the city, keeping critical systems alive, and learning the foundations that shaped who I am as an engineer today. Every console screen taught me something new and every problem strengthened my desire to help others through technology.

My Essential IT Troubleshooting Guide

In every company I have worked for, the tools that saved the day were not fancy dashboards but simple commands and fundamentals I could trust.
This is my personal troubleshooting arsenal, written so even a non technical reader can follow the logic behind what I do.

Each section answers three things
• What it is
• Why it matters
• How I use it in real life


Name Resolution Basics

A record

What
• A record is a phone book entry that says “this name belongs to this IP address.”

Why
• Users remember names better than numbers. If the A record is wrong or missing, they land in the wrong place or nowhere.

How I use it
• When a site is not loading, I ping the name and check if the IP address matches what we expect.
• If it does not, I fix the A record in DNS and wait for it to replicate.


CNAME

What
• A CNAME is a nickname that points one name to another name.

Why
• It lets you move services without breaking users. The public name stays the same while the target changes behind the scenes.

How I use it
• For services like autodiscover or app portals, I often see CNAMEs that point to Microsoft or another provider.
• When something breaks after a cutover, CNAMEs are one of the first things I verify.


DNS

What
• DNS is the global phone book that turns names into IP addresses.

Why
• If DNS fails, everything feels broken. Browsers, Outlook, file shares, all of them depend on DNS.

How I use it
• I run nslookup name.company.com to see which DNS server is answering and what IP it returns.
• If users in one site can reach something and other users cannot, I compare DNS answers between locations.


Hosts file

What
• The hosts file is a tiny local phone book on the computer.

Why
• It overrides DNS for that machine. One bad line can send traffic to the wrong place.

How I use it
• Location on Windows

C:\Windows\System32\drivers\etc\hosts

• I open it with Notepad as administrator.
• If someone hard coded a testing IP and forgot about it, I comment it out or remove it, then flush DNS.

Flush cache

ipconfig /flushdns


Nbtstat and TCP IP

What
• Nbtstat is an older tool for NetBIOS name resolution.
• Hard coded TCP IP means a manual IP instead of DHCP.

Why
• Nbtstat helps when legacy name lookups act strange.
• Hard coded IPs can cause conflicts or make VLAN changes painful.

How I use it
nbtstat -n to see local NetBIOS names.
nbtstat -c to see the name cache.
• When I find static IPs on client machines, I document them and move them to DHCP reservations so the network is easier to manage.


Network control panel shortcut

I still use this every week

From Run

ncp.cpl

It opens the Network Connections window so I can quickly check adapters, enable or disable, or look at IPv4 settings.


DHCP Essentials

What
• DHCP hands out IP addresses, gateways and DNS to clients.

Why
• If DHCP fails, users cannot get on the network or suddenly have duplicate addresses.

Best practices
• Use at least two DHCP servers where possible.
• Define scopes with correct gateway and DNS.
• Use reservations for printers and key servers.

Commands I use on clients

ipconfig /release
ipconfig /renew

If a user can reach the internet but not internal resources, I check that DNS from DHCP is internal and not a public resolver.


MX, Autodiscover and Mail Flow

MX record

What
• MX tells the world which server receives mail for your domain.

Why
• If MX points to the wrong place or has a low priority backup you forgot, email can vanish or queue.

How I use it
• I use MXToolbox to check MX records and verify that they point to Exchange Online or the correct email gateway.

Autodiscover

What
• Autodiscover tells Outlook where to find the mailbox and settings.

Why
• A broken autodiscover record means constant password prompts or profile creation failures.

How I use it
• I verify the Autodiscover CNAME or SRV record.
• I test with Outlook connectivity tools or Test-OutlookConnectivity when available.

Hunting spam engines and bad SMTP

Where malware hides
• In browser extensions
• In Outlook add ins
• In unknown services or scheduled tasks that send mail through SMTP

How I clean it without reimaging
• Check Outlook add ins and disable anything suspicious.
• Run msconfig and Task Manager to review startup items and tasks.
• Review SMTP logs on the server to see which host is sending unexpected traffic.


Certificates and SSL in Hybrid Environments

Internal web apps depend on trusted certificates so browsers know the site is safe. When an SSL expires, internal apps stop working and Chrome or Edge will show warnings.

Why we create new SSLs
• Internal web apps must be trusted.
• Intranet portals and legacy apps often stop working when an internal CA certificate expires.
• External issued certs from DigiCert or GoDaddy are trusted by browsers.

PowerShell to generate a CSR example

$csr = New-ExchangeCertificate -GenerateRequest `
-SubjectName "CN=mail.contoso.com" `
-DomainName "mail.contoso.com","autodiscover.contoso.com"
Set-Content -Path "C:\Certs\mail_csr.req" -Value $csr

After the CA signs it, import

Import-ExchangeCertificate -FileData ([Byte[]]$(Get-Content "C:\Certs\mail_cer.cer" -Encoding byte -ReadCount 0)) -PrivateKeyExportable $true

Enable for necessary services

Enable-ExchangeCertificate -Thumbprint <Thumbprint> -Services IIS,POP,IMAP

Where I keep it
• C:\Certs or another controlled folder
• Never leave certificates scattered in Downloads

Core servers
• I open Task Manager with Ctrl Shift Esc
• File, Run, then mmc
• Add the Certificates snap in and import there
Or I import directly with PowerShell.


Machine Trust Relationship Problems

When Windows says “the trust relationship between this workstation and the primary domain failed,” the computer account and the domain no longer agree.

On a traditional domain
• Disable LAN and WiFi
• Log in using cached credentials
• Reset the local admin password if needed
• Disjoin from the domain and put it in a workgroup
• Reboot
• Join it back to the domain

For Azure AD joined devices

Check status

dsregcmd /status

If broken

dsregcmd /leave

Then re join from Settings under Access work or school.


RDP Session Cleanup

Sometimes users cannot remote into their office desktop because a stale session is still connected.

I run from my admin machine

query session /server:192.168.10.25
logoff <SessionID> /server:192.168.10.25

After that, they can reconnect without rebooting the server.


Active Directory Tools

ADSIEdit

What
• A low level editor for Active Directory objects.

Why
• Last resort for fixing broken attributes or lingering records when normal tools cannot reach them.

How I use it
• Only with full backups and a clear change plan.
• I use it to clean up orphaned objects or legacy settings left behind.

Event Viewer

What
• The black box recorder of Windows.

Why
• Every blue screen, login failure, replication problem and service crash leaves a trace here.

How I use it
eventvwr.msc
• I focus on System and Directory Service logs on domain controllers, and Application logs on servers hosting apps.


FSMO Roles

What
• Flexible Single Master Operations are special AD roles for schema, naming, PDC, RID and infrastructure.

Why
• These make sure there is one source of truth for sensitive changes.

Best practice
• Know exactly which DC holds each role.
• Protect those DCs like crown jewels.

If a FSMO owner is gone forever
• You can seize the role to a healthy DC using ntdsutil.
• After seizing you never bring the old DC back online.

This is rare but every senior engineer should know the process in theory.


AD and Entra ID Health

On premise AD health

dcdiag
repadmin /replsummary
repadmin /showrepl

I always confirm
• DNS is correct
• SYSVOL is in sync
• Time is correct and within a few minutes across all DCs

Entra ID health

Connect-MgGraph
Get-MgUser
Get-MgDirectoryAudit

I check
• Sign in logs for failures
• Conditional Access for blocked locations
• Device compliance for machines that suddenly appear non compliant

AD controls computers and users on site.
Entra controls cloud identity and device trust.
In a hybrid world, both must be healthy.


Azure and Terraform

Azure CLI read only commands

az login
az account show
az group list
az vm list
az storage account list

These tell me what exists without changing anything.

Terraform for infrastructure as code
• Initialize the directory
terraform init
• Format
terraform fmt
• Validate
terraform validate
• Plan
terraform plan

Nothing changes until terraform apply is run.
For interviews, being comfortable with init, plan and validate already shows good understanding.


Microsoft 365 Services

Group Policy

Purpose
• Central control of security and settings for on premise joined machines.

How I create it
gpmc.msc
• New GPO
• Edit with the settings I want
• Link to the correct OU


Universal Print

What
• Cloud based printing that removes the need for classic print servers.

Why
• Easier management for hybrid and remote users.

I register printers in Universal Print and assign permissions based on groups, so users can get printers automatically.


SharePoint Online

Steps I follow
• Go to Microsoft 365 admin center
• Open SharePoint admin
• Create a new site
• Assign owners and members
• Set sharing and retention policies

This becomes the central place for team documents and intranet content.


OneDrive and Data Migration

OneDrive
• Sync client installed on machines
• Known Folder Move for Desktop, Documents and Pictures
• Version history to protect from mistakes and ransomware

Migrating data
• I prefer SharePoint Migration Tool or Mover.
• I clean old data first so I do not carry garbage into the cloud.
• I communicate to users what will move and what will not.


Why This Arsenal Matters

These are the tools I have relied on in city government, banks, energy drinks, and manufacturing.
They are not fancy, but they work.

Every time I help a user reconnect, restore a service, or clean up a broken configuration, I am really doing three things

• Protecting the company and its data
• Supporting my teammates so they are not alone in the fire
• Honoring the gift God gave me to understand and fix complex systems

This arsenal is how I serve.
Whether I am helping a small office or a multi site enterprise, the pattern is the same ask good questions, run the right checks, fix the root cause, and leave clear notes so the next engineer can see the path.


© 2012–2025 Jet Mariano. All rights reserved.
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