This bug has been added to the tracker:
https://winscp.net/tracker/786

I have sent you an email with debug version.

arf_uk wrote:

On v5.0.4 I'm still seeing this issue.

I've a mix of password sessions and saved keys but regardless everytime I initiate a transfer, I still get the problem.

Additionally on 5.0.4 I still get the Invalid Access to memory error on start up.

I can confirm that I still get these issues on 5.0.5.

Regardless, every time I initiate a transfer, I always get re-prompted for a password.

On v5.0.4 I'm still seeing this issue.

I've a mix of password sessions and saved keys but regardless everytime I initiate a transfer, I still get the problem.

Additionally on 5.0.4 I still get the Invalid Access to memory error on start up.

dlong500 wrote:

I'm using 5.0.4 and having this problem. Note that I am NOT using keys or passphrases but simple password authentication.

I have the "Remember password of main session for background transfers" checked, but the first time I transfer a file after opening a session I get prompted for the password again.

This is definitely changed behavior from the 4.x versions I was previously using.

Can you send me an email, so I can send you back a debug version of WinSCP to track the problem? Please include link back to this topic in your email. Also note in this topic that you have sent the email. Thanks.

I'm using 5.0.4 and having this problem. Note that I am NOT using keys or passphrases but simple password authentication.

I have the "Remember password of main session for background transfers" checked, but the first time I transfer a file after opening a session I get prompted for the password again.

This is definitely changed behavior from the 4.x versions I was previously using.

WinSCP does not keep the passphrase in memory.
You can use pageant for that.

arf_uk wrote:

I get the Invalid Access to Memory bug and the behaviour I notice is that it resets my local directory back to the installation directory. Hope this helps.

I'm sending you an email with debug version.

I should make this clear, that I'm using SSH key based authentication, and the password i'm being prompted for on every transfer is my SSH passphrase.

Sorry should have been clearer initially.

Using 5.0.2 on WinXP SP3 - running in 'Commander' mode.

I have 'Remember password of main session for background transfers' checked in the options, but all background transfer are causing prompts for password when carried out.

Also

I get the Invalid Access to Memory bug and the behaviour I notice is that it resets my local directory back to the installation directory. Hope this helps.