Note: I have not experienced problems with auto-typing passwords into the RDP 'Windows Security' dialog when logging into local or remote servers (e.g. If you can't see what characters are being typed, you may still be able to identify the characters through judicious selection of delays (above).
Use combinations of all workarounds to find a combination that works or to probe the problem. Are you using a recent computer or could there be CPU performance issues?. Is there anything unusual about the passwords e.g. Does the problem affect certain connections reproducibly, or all connections? If so is there any feature that is common to the logins that fail or succeed?. Are the same portions of the password lost each time? (if you can tell). 
Are the same number of characters lost each time? Fixed issue sending Ctrl-Alt-Del in RDP when set to on remote computer keyboard. I integrated one of the suggestions from the comments, but it's been too long for me to remember which one.Is the problem random or systematic? e.g. Note: I believe his command and mine differ slightly. You can watch them come and go under Windows Credentials -> Generic Credentials. Read Adam's tutorial for the full details, but basically it uses Windows Credential Manager to store the credentials for 5 seconds while the RDP window launches, and then remove them. Now, when you add a server, enter the URL as rdp:// Type "rdp" in the schema box, and past the snippit below into the URL Override box. Tools -> Options -> Integration -> URL Schema Overrides -> add I believe there is also now a plugin for KeePass to launch RDP sessions, but this still works great for me. 
Here's the original tutorial, all credit goes to that author, Adam Plocher. There's a way to launch RDP sessions with KeePass, making it much easier for sysadmins and the like to log into servers they have access to. I'll add this to it's own post, instead of my KeePass tutorial, since it's a more advanced feature.
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