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If we try to derive the corresponding declarative form of the question:

How long ago was it since he had slept without fear?

we will find:

It was X since he had slept without fear.

where X, the amount of time we're asking about, is replaced by How long ago in the question form.

Now, if we try to do the same with:

How long ago was it that he had slept without fear?

we will get:

It was X that he had slept without fear.

But I don't think the construction above is grammatical, or is it?

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The first example is incorrect:

(!) How long ago was it since he had slept without fear?

"Since" and "ago" are separate and mutually exclusive constructions. Also, the past perfect ("had slept") should not be used because the main verb is not in the past perfect. Use the simple past instead. You can say:

How long ago was it that he slept without fear?

Or

How long has it been since he slept without fear?

Or, if the past perfect is really what you want, the main verb must also be changed so the tenses agree:

How long had it been since he had slept without fear?

Your last sentence is indeed not grammatical:

(!) It was X that he had slept without fear.

You can say any of these:

  • It has been X since he slept without fear.
  • It had been X since he had slept without fear.
  • He hasn't (or hadn't) slept without fear for X.
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    I don't think OP is asking about tenses though. The problem is just that the declarative version is missing ago - correcting the tense as above it would be e.g. it was 5 years ago that he (last) slept without fear. – user96060 Jun 26 '19 at 22:29
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This: How long ago was it since he had slept without fear? [This is past perfect]

may be said like that but would more easily be said like this:

How long had it been since he had slept without fear? (or: without feeling scared)

Declarative form: It had been four months since he had slept without feeling scared. [past perfect]

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