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Hi Hugo,
Greetings!

There is some strange behaviour when URL Rewriting is used with aliases.

Hiawatha doesn't check for "exists" in the aliased path.
The setup that I have is:

WebsiteRoot = /usr/share/squirrelmail
Alias = /nss:<path to wordpress>

this caused issues with the index page returning 404 for any url having "?" in it.
I am using the url rewrite provided by you with "/nss" added to everything.

UrlToolkit {
    ToolkitID = my2
    RequestURI exists Return
    Match ^/nss/.*\?(.*) Rewrite /nss/index.php?$1
    Match ^/nss/.* Rewrite /nss/index.php
}

Currently, I had to make a softlink form /usr/squirrelmail/nss to my wordpress installation for it to work.
I am not sure if it is a bug or it is intended behaviour.

Hiawatha version: 9.2
Operating System: Debian7

It is true that Hiawatha doesn't look at aliases when processing UrlToolkit rules. It is intended behaviour.

Is there any other work around that you would suggest?
Regards

Create a softlink to the other directory.