He may regret having quit his job.

Does this mean

It is possible that he now wishes he hadn't quit his job.


It is possible that he will eventually wish he hadn't quit his job.



He may regret having quit his job.

That 'may' indicates a form of modality that has to do with possibilities, called epistemic modality. In other words, 'may' shows how much the speaker believes in what they're proposing in their sentence.

However, both of your proposed interpretations are possible, since there isn't a location in time specified. He may regret the decision now, or in the future.

If the speaker needs to highlight that the time of regret is possibly now, they can use the progressive aspect:

He may be regretting having quit his job.

. . . or include "now" in the original sentence. Perfect can be used to indicate the action being done in the past:

He may have regretted having quit his job (already).

To point to future, simply an inclusion of "in the future" in the original sentence would suffice.

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He may regret having quit his job.

could also be written:

Having quit his job, he may regret it.

Having quit his job means that he already quit.

Having considered your question, I decided to write an answer.

I completed my review of your question before answering.

The possibility part, introduced by may, only involves regret, and has no function in the timing of events.

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