Remember when you customise any file and place it in CustomUpdate to use the same filename, only appending the trunk name and 1 or 0 (for https or http) to the name and nothing else. If you so change the filename, update the rules in the trunk Advanced Settings URL Set: find the rule that affects the file you changed, copy it (placing it directly below) and modify the new rule to include your filename. GIYF when it comes to Regex++ expressions used in UAG if you are using strange filenames.
You need to modify every trunk if you change a major file like login.asp if they all use that file. If you have a custom naming convention so each trunk has its own version of the file, you might be able to write one rule that matches all your names and use that in each trunk, or you might have to write a rule from scratch on each trunk.
[GIYF: Google is your friend]
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