Me too; it’s all but impossible to type in the vast majority of my passwords because they are 40 or more completely random characters (well, alpha numeric - a lot of sites don’t allow arbitrary symbols, or do allow them then break.)
In the past when apps have managed to prevent use of my password manager I have been forced to change the password; I change it to “password” or some variation (p@assw0rd normally satisfies all the stupid requirements) then change it back when the problem is fixed.
One particularly bad, notorious, example is Inituit’s “TurboTax” program. For years they have insisted that you type in the the password of your brokerage accounts - they block copy/paste and don’t support password managers. This forces users with brokerage accounts to change from a secure password to an insecure one when doing their taxes using the program - Intuit are the EdgePark of finance, they insist it’s the brokerage firms requiring this but, curiously, Intuit do it everywhere.
I don’t use t:connect, but I regard a bug like this as a show-stopper. Forcing people to use insecure passwords in this way is the lowest of the low.
Afflicted people might like to try a password manager; look at Dashlane or LastPass, both offer permanently free implementations with limited functionality. Make sure to immediately cancel the “premium” trial with LastPass to avoid billing, it may be necessary to do the same with DashLane.
These programs are keyed in to the mobile phone accessibility support and behave as a keyboard; you can copy/paste the passwords if you want but you can also just have the password manager type them in. It is possible that iOS now supports this natively; it does offer to store passwords but I don’t know if this is just for browser apps. I don’t use it; the password managers work fine with the browsers and are cross platform (though you may have to pay for that.)
With a password manager repeated entering of the same password gets down to a single click. It’s still a PITA but it no longer matters how secure, or rather how insecure, the password is.
On Windows the fix for apps that block copy/paste is a utility called AutohotKey: https://www.autohotkey.com/ Similar programs exist for other operating systems (see the end of the wikipedia article). These programs support scripts which can use OS features to inject keys into the app as though they were typed - this is an essential requirement of some accessibility support. Appropriate scripts grab the copy’n’paste buffer contents and type them in, bypassing attempts to ban “paste” in the app.