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I am using Sitecore XC 9.3 and am often get the following error after a system start:

Application 'MACHINE/WEBROOT/APPHOST/DEFAULT WEB SITE'
                     with physical root 'C:\inetpub\wwwroot\' created process
                     with commandline
                     'C:\inetpub\wwwroot\Sitecore.Commerce.Engine.exe ' but
                     failed to listen on the given port '39597'

I did not have this problem with earlier version of XC.

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After debugging the SQL connection, it turns out that the Commerce Engine makes a database call in the application startup. This first call can take quite some time, and sometimes even more than 2 minutes.

As 2 minutes is the default startupTimeLimit (see https://docs.microsoft.com/en-us/aspnet/core/host-and-deploy/aspnet-core-module?view=aspnetcore-3.1), IIS will kill and try to restart the application.

Workaround is to enlarge to timeout in web.config to e.g. 10 minutes:

...
<aspNetCore ... startupTimeLimit="600" />
...
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