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I am trying to make/modify a custom syntax file to highlight errors and successes in my Arcserve tape backup logs. While I can get single keywords like fail, start, incomplete etc. to show highlighted in different colors, I can't seem for the life of me get a string of words like

Start Backup Operation

to show up.

Is this possible or am I barking up the wrong tree? Any examples of the correct syntax would be great!

I don't think that you can highlight strings but only individual words.
You could make Start, Backup and Operation all keywords and make the keywords case sensitive. This would highlight the phrase but also any other occurrence of the individual words. Can you live with that?