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The example is mine.

Sorry for not sending you the report on time. Last working week was so hectic and unproductive that on Saturday I needed to catch up on my backlog. Only on Sunday did I remember that I was supposed to have sent the report on Friday morning.

Should I use "I was supposed to send" or "I was supposed to have sent"?
What would be the difference between the two?

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Only on Sunday did I remember that I was supposed to have sent the report on Friday morning.

The deadline was over at the point of the discovery (Sunday). So to have sent is correct.

To send is used if the deadline was still not over on Sunday.

I was busy last week. Only on Sunday did I remember that I was supposed to send the report the following Monday. Here is the report.

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  • I agree that to have sent expresses the retrospective view; however, to send shoudn't be considered incorrect. It's just a different temporal perspective: I was expected to send....or I had to send... Commented Jun 28 at 13:09
  • I say it a lot: Language is expressive. It's not the factual world talking through the medium of mindless speakers, or people having to conform to objective reality, but people expressing their subjective take on the world. The speaker who doesn't express the situation retrospectively using the perfect could be remembering what they (as yet) had to do when doing it would still have been timely, and the fact that time has passed and they have missed their deadline might find expression in their tone of voice (prosodically) rather than in the choice of verb, with heavy emphasis on Friday. Commented Jun 28 at 13:17

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