Same thing here. Use Toad instead. It sucks less. And it can sort, something I found lacking in Mgmt Studio.

I have the same problem, and some of my colleagues too. Searching tells me that some have the same problem and some doesn't experience it at all.

Microsoft has been aware of this for two years or more, but so far it doesn't appear to be a solution...

MSDN Forums "SQL Server Management Studio 2005 forgets password?"

Here's someone why had some luck by typing in the server name instead of selecting it in the dropdown. (I haven't tried this myself yet.):

eggheadcafe "Management Studio forgets password ("change connection")"

Here's a bug report from 10/2006 that is closed because it's a duplicate, but I haven't been able to find the original bug report...

Microsoft Connect: "'Remember Password' option is not remembered in Registered Server Properties"

It's 2015 and I have the same problem with SQL Server 2012 Management Studio.

If you're not going to fix something, then remove it.

I wonder if they have PsyOps programs at Microsoft....LOL :)

Here is my workaround that I have been using for years. It requires me to run a batch file shortcut on my desktop every morning before I start SSMS. First you must have a good working set of logins and passwords. That requires you to find any and all connections that you want to be remembered. Once you have done this, make a copy of the "SqlStudio.bin" file that contains the logins and passwords to "SqlStudio - Copy.bin". Now you can run the following batch file, I call "PwdFixSSMS.bat". Here is the batch script and change the "YOURNAME" in the third line to your directory usually your login. Hope this helps;

@echo off

REM:: fixes lost passwords in SqlStudio (SSMS) Then Open program (optional)

cd C:\Documents and Settings\"YOURNAME"\Application Data\Microsoft\SQL Server Management Studio\11.0

copy "SqlStudio - Copy.bin" SqlStudio.bin

rem:: Start "" "C:\Program Files (x86)\Microsoft SQL     Server\110\Tools\Binn\ManagementStudio\Ssms.exe"

start %comspec% /c "mode 60,10&title My Popup&color 1e&echo.&echo. Restored SMSS Password File SqlStudio.bin %date%&echo.&echo.&timeout /T 2"