There are many possible causes for this. This answer is more a list of things to look into than a set of solutions. If your terminal windows suddenly began starting slowly after a Cygwin upgrade, the most likely cause is that you have an outdated authentication setup. For almost all its lifetime, Cygwin has used Unix-like /etc/passwd and /etc/group files to mirror the contents of the Windows SAM and AD databases. Although these files can still be used, since Cygwin 1.7.34, new installations now use the SAM/AD databases directly. To switch to the new method, move these two files out of the way and restart the Cygwin terminal. That runs Cygwin in its new default mode. If you are on a system that isn't using AD domain logins, this makes Cygwin use the native Windows SAM database directly, which may be faster than the old method involving /etc/passwd and such. At worst, it will only be a bit slower. (Which situation applies depends on the benchmark you run.) If you are on an AD system, a hybrid approach you might consider is to re-run mkpasswd and mkgroup, then put the following into /etc/nsswitch.conf to make Cygwin treat these files as read-only local caches of your AD database: passwd: files group: files By leaving out the "db" option, we are telling the Cygwin DLL not to even try to do AD lookups. If your AD servers are slow, this local cache will speed things up. The downside is the old stale cache problem: any time the AD databases change, your local cache will go out of date until you update the files manually. Another common cause of slow Cygwin Terminal starts is a bad DNS setup. Many things that occur during a Cygwin Terminal startup require fast DNS lookups. More...? If none of the above helps, the best troubleshooting method is to run your startup scripts in debug mode. Right-click your Cygwin Terminal icon, go to Properties, and edit the command. It should be something like C:\cygwin\bin\mintty.exe -i /Cygwin-Terminal.ico -. Assuming you are using Bash for your login shell, change it to C:\cygwin64\bin\mintty /bin/bash -lx That will cause it to write out a line for every command it runs. A slow Cygwin Terminal launch usually means one or more of the many commands Cygwin runs when starting up will take a long time. That will be your clue as to what's going on.