Microsoft office offers an inhouse tool SCANPST.EXE, which can scan, diagnose, and repair errors in your Outlook data file. Read: Excel, Word or PowerPoint couldn’t start last time Do you want to start in safe mode? 3] Repair data file Here you can unselect the addons you want to disable and relaunch Outlook.
At the bottom of this section., click on the Go button next to Manage Comm Ad-ins. Select the Add-ins section, and it will reveal the list. Click on File > Options to open the Outlook Options window. You can either disable everything and then it on one by one or, you can disable one and relaunch Outlook to check if everything is working fine. If you had set up a password, then make sure to provide that. Select the default profile, and then click ok. It will then prompt you with Choose Profiles. If you want manually start Outlook in safe mode, then first close it, and then type and press the Enter key the following the command Outlook /safe If Outlook works fine in this mode, then your problem could be with add-ins, profile, and other configuration. When Outlook launches in safe mode, it disables anything which is not necessary. It is a good idea to choose, yes, when you get the Outlook Safe Mode prompt. Otherwise, it will be challenging to figure out what was causing the problem. Make sure you perform each step and then check if you still have issues. 
We will have to check on what is causing the issue.
The error means that Outlook was not able to open in a properly i.e., loading profile, addons, and configuration files. Safe mode could help you troubleshoot the problem, but some features might not be available in this mode. When you launch Outlook, and you receive an error message saying “Outlook couldn’t start last time” and asks you to launch it in safe mode, then this most can help you resolve the problem.
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