Trouble with a workflow working properly

I have a workflow set up to send an email to USEREMAIL when the contents of a field match the conditions of “Simple Estimate” or “Detailed Proposal”. There is an action then that looks for the contents “Simple Estimate” or “Detailed Proposal” and changes the contents to “Sent”. This used to work fine, but just stopped working about a month ago.

I “patched” it by adding double quotes to the criteria in the workflow "“Simple Estimate” or ““Detailed Proposal”” but now it when either “Simple Estimate” or “Detailed Proposal” is selected it sends two emails to USEREMAIL. One has the estimate and one has the proposal. Any ideas? It’s really plugging up our Inboxes by sending both emails. And its confusing.

Thanks in advance.

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