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  1. Sheila continued to work after she had her baby. (Longman Online)
  2. Silvina continued to work after she had had her baby. (Longman Contemporary)

I would guess that 1 implies Sheila continued her work, pregnant. 2 Silvina continued her work after bearing her child. Are my guesses all right?

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Are my guesses all right?

Not exactly.

Sheila continued to work after she had her baby.

This is the simple past, and it means that she continued work after bearing her child. In English, we use have a baby idiomatically to refer to the act of birthing. Since it's in the past, it means the birthing is complete, and after tells us she did not continue working until after that. The two events are grossly contemporary, both being at some point in the past. Sheila returned to work relatively* quickly; there was no extended period of absence, though we don't know how precisely long it took.

Silvina continued to work after she had had her baby. (Longman Contemporary)

This also means that she continued to work after bearing her child. However, the use of past perfect places the two events at greater remove by indicating they occurred at different times; the past perfect event occurs distinctly before the simple past event. With the simple past, it's possible for the two to happen consecutively, but not so with the past perfect. It's a subtle difference, but we can infer that the time between child birth and continuance of work is likely considerably greater than in the first example. Here, Silvina did not immediately return to work after having her baby; some non-trivial amount of time passed, though we don't know how much.

* - Relatively means different things to different people, and when said about different people. I'm being intentionally vague. We often play a bit loose with the language and depend on the context for nuances. A week's leave to recover from childbirth might be unusually long for one woman (maybe she really loves her work); conversely, a month's might be not nearly long enough for another (perhaps her job requires strenuous physical labor).

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    I wonder, do people use such "had had" constructioins in real life conversations, or are they used predominantly in literature.
    – CowperKettle
    Aug 11, 2014 at 6:44
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    A good question. I mostly hear a different usage of had had, for past irrealis conditionals (e.g. if I had had the time). Using the past perfect in general to specify timeframes is much less common conversationally in my experience. Probably because we often play fast and loose with the language when speaking colloquially, relying more on implication and tone to express nuances.
    – Esoteric Screen Name
    Aug 11, 2014 at 6:47
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    @CopperKettle, "had had" is used all the time in speech. Try a "spoken" search for it in COCA. You will get lots of hits. I think it actually works better in speech than in writing. It looks kind of weird in writing. Some people (not me) avoid it in writing for that reason.
    – Dangph
    Aug 11, 2014 at 8:40
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    It's debateable here whether dropping the first 'had' is a deliberate attempt to change the verb tense, or whether it is simply a result of the pronunciation difficulty of 'had had' and/or the 'tense difficulty' of past perfect, which in my experience people will avoid whenever they can. I have found that it is more common for speakers to drop the 'had' (without necessarily changing the meaning) when the main verb has the same form in past simple and past participle (regular verbs and AAA or ABB irregulars): e.g. 'She went to bed after she had set the alarm' > 'after she set the alarm'.
    – Sydney
    Aug 11, 2014 at 11:01
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    Yes, it's heard in colloquial usage. It would be spoken more as “After she’d had her baby.”
    – Micah Walter
    Aug 11, 2014 at 13:00
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In both cases, nothing is said or implied about working during pregnancy.

The simple past in [i] makes the "having a baby" a "continuous", prolonged action, so we are not so much focussing on the actual childbirth, but rather on the fact that she became a mother (and the responsibilities that come with that).
You could rewrite that sentence as:

[i] Sheila continued to work when she became a mother.

When we are talking about Sheila's life and career, this would be a common way of telling the audience that she didn't give up her career for her child.

The second one focusses on the actual (momentary) act of having a baby, so the moment of childbirth. This sentence would be more likely used in a situation where we explain since when Silvina has started working again (after her pregnancy leave?):

John noticed that Silvina was back in the office. I told him that she continued her work after she had had her baby.

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