Expression "had to have done"

[Lost_Soul]

Hi, dear teachers !

Could you answer these few questions:

1. does I had to have taken an umbrella mean the same as I should have taken an umbrella?

2. does I didn't have to have taken an umbrella mean the same as I needn't have taken an umbrella?

Thanks in advance !

[Mister Micawber]

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To me they mean:

1-- had to have taken = must have taken
2-- The negative sounds too awkward to live. To negate #1, 'I must not have taken'; otherwise, your option-- 'I needn't have taken'.

There may be other opinions.
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Native English teacher at Mister Micawber's

[Edison_Chen_e_c]

In my opinion, the first one I won't say it's completely the same, and the second one I think it's nothing different between the two.

1.I had to have taken an unbrella.

I had to take an unbrella with me then as it was raining.
I had to/must/should have taken an unbrella with me when still at home then as it seemed to rain.

(1)In the first sentence, I just describe something that I had to take one as it was raining.
(2)In the second sentence, I blamed myself since I didn't take one with me when going out.
(3)The mood(tone) of 'had to/must' is stronger than 'should' and with different meanings.

2.I didn't have to have taken an umbrella.
Like Point #1.

Your sentence looks fine, but I am thinking if we could use 'must' and 'need' instead of the past tense 'did not have to'.

Any opinions?

[Lost_Soul]

Hi, Mister Micawber

Thanks a lot to you !