It will never be entirely random. Some range more than likely. You may be able to restrict the range. You could certainly set stunnel up for each “random” port. E VICS, LLC Eric S Eberhard 2933 W Middle Verde Rd Camp Verde, AZ 86322 928-567-3727 (land line) 928-301-7537 (cell phone) http://www.vicsmba.com <http://www.vicsmba.com/> https://www.facebook.com/groups/286143052248115 From: stunnel-users <[email protected]> On Behalf Of Brent Kimberley Sent: Friday, June 26, 2020 4:11 PM To: Thomas Ward <[email protected]>; [email protected]; Coviello, Paul <[email protected]> Subject: Re: [stunnel-users] winsock permissions issue (i.e. WSAEACCES 10013 / 0x271D) What are you trying to accomplish? I.e. Is TLS the best wrapper for the job? (i.e. TCP over TCP.) On Thursday, June 25, 2020, 11:44:38 a.m. EDT, Coviello, Paul <[email protected] <mailto:[email protected]> > wrote: Maybe, I also just found out that the port it goes out is not what I thought it was. It’s a random port. Not sure if it’s doable now. Thanks for your help