Email is down, you have got three deadlines today, and Outlook is giving you nothing but a spinning wheel. We get it. Email issues make up about 1 in 4 of all our support tickets, so this is something we deal with every single day.
Before you pick up the phone, here are the things we would check first if we were sitting at your desk.
Start here - these fix more than half of Outlook issues
1. Close Outlook and reopen it
Not minimise. Close it properly. Right-click the Outlook icon in your taskbar and choose "Quit Outlook" or "Close window." Wait 10 seconds, then open it again.
This sounds obvious. But a surprising number of Outlook problems are caused by the application getting into a bad state - a stuck sync, a frozen process, a failed connection attempt that never timed out. Closing and reopening clears all of that.
2. Restart your computer
Yes, really. If you have not restarted your machine in a week, this alone might fix it. Windows accumulates temporary files, background processes, and memory issues that a restart clears out.
We see machines that have been running for 30+ days without a restart. Outlook is particularly sensitive to this because it depends on several Windows services and network connections that can all degrade over time.
3. Check your internet connection
Open a web browser and try loading a website. If the browser works fine, your internet is not the problem. If the browser is also struggling, Outlook is not the issue - your network is. Restart your router, check your WiFi connection, or try plugging in with an ethernet cable if you have one.
For businesses on fibre in Cape Town, this can sometimes be a provider issue. If multiple people in the office are affected, check with your fibre provider before troubleshooting individual machines.
If the quick fixes did not work
4. Check if Outlook is stuck "trying to connect"
Look at the bottom-right corner of the Outlook window. If it says "Trying to connect..." or "Disconnected", Outlook cannot reach your mail server.
Try this:
- Click the "Send/Receive" tab at the top
- Click "Work Offline" to toggle offline mode on
- Wait 5 seconds
- Click "Work Offline" again to toggle it back off
This forces Outlook to drop its current connection attempt and try a fresh one. It works more often than you would expect.
5. Clear your Outlook cache
Outlook stores a local copy of your emails in a file called an OST file. Sometimes this file gets corrupted or bloated, and Outlook slows to a crawl or stops responding entirely.
To find and manage this:
- Close Outlook completely
- Open File Explorer and paste this into the address bar: %localappdata%\Microsoft\Outlook
- You will see one or more .ost files. Note their sizes.
If your OST file is very large (over 10GB), that could be the problem. Renaming the file (add ".old" to the end) and reopening Outlook will force it to create a fresh copy by downloading your email again from the server. This takes time but often resolves persistent Outlook issues.
A real example from our tickets: One of our clients reported "Outlook won't open." When we investigated, we found 14 .ost files totalling around 200GB. The machine simply could not handle the load. We cleaned up the old files and had Outlook working again the same day.
6. Run the Microsoft Support and Recovery Assistant
Microsoft has a free tool called SaRA (Support and Recovery Assistant) that diagnoses and fixes common Outlook problems automatically. Search for "Microsoft Support and Recovery Assistant" and download it from Microsoft's website. It runs a series of checks and can fix authentication issues, profile corruption, and configuration problems.
This is the same tool we sometimes use as a first step when diagnosing Outlook issues remotely.
Sometimes it is not Outlook at all
A few situations that look like Outlook problems but are actually something else:
Your Microsoft 365 account is locked or expired
If your organisation uses Microsoft 365, your account might have been locked due to a failed password change, an expired subscription, or a security alert. You will see Outlook asking for your password repeatedly, or refusing to connect even though the internet works fine.
Check with whoever manages your Microsoft 365 environment. If you are not sure who that is, that might be part of the problem.
Your mailbox is full
Microsoft 365 mailboxes have storage limits. When you hit the limit, you can receive email but not send. Or you cannot do either. Outlook usually shows a warning, but it is easy to miss.
Check your mailbox size: click File, then "Mailbox Settings" or check the bar at the bottom of your folder list. If it is over 90% full, you need to archive or delete old emails.
A Windows update broke something
This happens more often than Microsoft would like to admit. A Windows update can change settings, break add-ins, or conflict with Outlook's configuration. If Outlook was working fine yesterday and is not today, and you noticed your machine updated overnight, that is probably why.
Starting Outlook in Safe Mode (hold Ctrl while clicking the Outlook icon) disables all add-ins and loads Outlook with default settings. If it works in Safe Mode but not normally, an add-in or recent update is the culprit.
Your email server is down
If everyone in the office is having the same problem at the same time, it is almost certainly not your individual machine. It could be your email server, your Microsoft 365 tenant, or even a broader Microsoft outage. Check the Microsoft 365 Service Health page or ask a colleague if their email is working.
How to know when it is time to call IT support
You have tried the steps above and Outlook is still not working. Or maybe the issue is more complex than a single frozen application. Here is when professional help saves you time and stress:
- The problem keeps coming back. You restart, it works for a day, then freezes again. Recurring Outlook issues usually point to a deeper problem - a failing hard drive, a corrupt user profile, or a server-side issue that a restart cannot fix.
- Multiple people are affected. If it is not just you, the problem is likely on the server or network side. That is not something you can troubleshoot from your desk.
- You are seeing security warnings. Outlook asking for your password repeatedly, strange emails in your sent folder, or messages you did not write are potential signs of a compromised account. Do not ignore these.
- You have lost emails. If messages are disappearing, not arriving, or showing as sent but never reaching the recipient, there may be a mail flow issue that needs someone with access to your email configuration.
- It has been more than an hour. Seriously. If you have spent an hour on this and it is not fixed, the remaining causes are not things you are likely to resolve yourself. That hour of your time has a cost, and it is almost certainly more than the cost of a support call.
Why email breaks more than anything else
Email is the most-used business application, and it depends on more moving parts than most people realise. Your email client (Outlook), your operating system (Windows), your internet connection, your mail server or Microsoft 365 tenant, DNS records, security software, spam filters - any one of these can cause problems.
Email issues account for about 24% of all our support tickets. That is nearly 1 in 4. The next most common category (network and connectivity) comes in at 12%. Email breaks twice as often as anything else.
That is not because email is badly designed. It is because it sits at the intersection of almost every other system in your business. When any of those systems have a hiccup, email is usually the first thing you notice.
This is also why we built email security and continuity into our managed plans. Not just to protect against phishing and spam, but to keep email accessible even when something goes wrong with your primary mail server.
Still stuck?
If you have worked through these steps and Outlook is still not playing along, give us a call. We handle email problems every day, and most of them are resolved the same day.
Call: 087 820 5005 WhatsApp: 081 526 1626
Not an emergency? Get in touch and we will get back to you during business hours.
If your business keeps running into email issues, it might be worth looking at a managed plan that includes email monitoring and security. See what's included.
0 Comments