I’ve had contract roles extended multiple times without compensation changing, and it made me wonder when it’s appropriate to push for a rate increase. How do you approach negotiating pay when a temporary role becomes longer-term?

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Wait until they bring up extending the contract. That's always worked fine for me. Just come up with something based on the work you've just completed to justify it. "Based on the complexity of XYZ and the time it takes me to complete...."

When they extend a contract, that is usually a good time to ask for a raise. It is a bit awkward, though, because if they say no and you don't have anything else lined up, you kind of just have to go with it. But it never hurts to ask in my opinion.

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