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Help Desk Course | Outlook – Troubleshooting

Special thanks to our member for creating this content: John Korduba

Main Course Content Page




Why does a separate login display for Outlook?

Outlook won’t open

Outlook not receiving emails

Where are you connected to the internet?

User is not getting emails – more solutions

Engineer wants to know Outlook’s current connection settings

Outlook crashes every time you open it

How do I troubleshoot Add ins?

How can I re-create the Profile?

Exporting files


Here we look at some issues regarding Outlook that you may face as a Help Desk tech.


Why does a separate login display for Outlook?

Scenario: We have already created a client machine. Then we downloaded Windows 10 and Microsoft 365 to it. We closed the machine.

Now it’s a new day and we want to launch 365, specifically Outlook.
(Win10 desktop displays)

Search for the Outlook app…

… and click on it.
(“Outlook” log in screen displays)

At this point, user logs in with credentials.

Question: If we already downloaded Microsoft 365, why does a login screen come up when we launch Outlook?

Answer: Typically, the sys admin creates an account for the user in Active Directory and the account is synched with the cloud (365). However, here the scenario is that this is a small company with only a cloud account, no AD.

Outlook won’t open.

Question: User tries to launch Outlook repeatedly, but it doesn’t open. How to trouble-shoot?

Answer: It might be that the user has tried clicking on Outlook too many times, so too many instances are running. (see step below)

Open Task Manager.

It might be that Outlook has been opened multiple times. You would close all the instances and then have user launch it again.

Right-click each Outlook instance/click End Task.

Outlook not receiving emails.

Question: User says that Outlook is open, but they’re not getting emails. What to do?

Answer: If you check the bottom of the screen below, you’ll see that the user is “Working Offline”.

Click Send/Receive tab.
(Notice that “Work Offline” button is enabled.

Click Work Offline.
(“Working offline” mode is toggled off;
“Connected to Microsoft Exchange” now displays at bottom of screen).

Where are you connected to the internet?

Question: How can you determine what server you are connected to?

Answer: See steps below.

Click File menu
(“Account Information” screen displays)

In Account Settings area, link to server displays.

User is not getting emails – more solutions

Question: User’s Outlook is online, but emails are not being received. What else to check?

Answer: Try user’s OWA account. Are emails coming in there?

NOTE: Re-start Outlook. This solves many issues.

Engineer wants to know Outlook’s current connection settings

Question: An engineer wants to know the user’s Outlook connections. Where are these?

Answer: see steps below.

In the system tray, click the Hidden items icon (upward pointing triangle).

Click Outlook.
(menu displays)

Instead of clicking the Outlook icon (as per above), click Ctrl+Outlook icon.
(menu with more options displays)

Click Connection Status.
(“Outlook Connection Status” screen displays).

Engineer might ask for the Req/Fail # or some other information from this screen.

Outlook crashes every time you open it.

Question: Every time user opens Outlook, it crashes. How to eliminate the possibility that an add in may be the cause?

Answer: Open Outlook in Safe mode. (Steps follow).

Click Start/Run.
(“Run” dialog box displays).

Enter “Outlook /Safe” and click OK.
(Outlook starts in Safe mode).

If Outlook opens successfully in Safe mode, it means that an Add in is the problem.

How do I troubleshoot Add ins?

Question: If its determined that an Add in is the problem with Outlook crashing, how to troubleshoot this?

Answer: You have to isolate the particular add in. (steps follow).

Click File/ Options/ Add ins
-Ensure Manage drop-down has “COM Add-ins” selected.
(“Add ins” display)

At this point, you would try to isolate which Add -in is causing the problem and disable it.

How can I re-create the Profile?

Question: You’ve tried simpler solutions, but Outlook is still not working right. Now, let’s try re-creating the profile.

Answer: See following steps.

Ensure Outlook is not running.

Access Control Panel.

Change the View to Small Icons.

Click Mail (Microsoft Outlook 20xx).
(“Mail Setup” dialog box displays.)

Click Data Files.
(“Account Settings” screen displays)

Click Open File Location.
(Folder with Outlook profile displays).

At this point, you could delete the profile file and re-start Outlook. Outlook would then create a new profile, which should solve any problems. (NOTE: Instead of deleting the Profile file, you can just rename it and keep this file on your desktop, in case it needs to be restored.)

Here is an alternative way of dealing with a faulty profile file. Instead of deleting or renaming the Profile file, at this point…

Click the Up arrow (next to the Path area)…

…to go back one folder up.

(“Outlook” folder is selected.)

Cut the Outlook folder; paste it to your desktop for safekeeping.

Re-start Outlook – a new profile gets created. (Hopefully this solves the issue).

Exporting files

Question: How do I export Outlook files?

Answer: See following steps.

Click File/ Open and Export.
(“Open” screen displays).

Click Import/Export.
(“Import and Export Wizard” displays).

Select Export to a file.

Click Next.
(“Export to a file” dialog box displays).

Select Outlook Data file (pst).

Click Next.
(“Export Outlook Data File” dialog box displays.

Select folders to be exported.

NOTE: Exporting an entire mailbox could take some time.

Click Next.

Follow the prompts to complete the process.

Special thanks to our member for creating this content: John Korduba

Main Course Content Page

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