Should we pronounce the second d in "didn't"? What happens to the sound, phonetically speaking?
In British English it seems to merge with the n to produce something which isn't on the standard phonetic chart- as far as I can tell.
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"Didn't" has two syllables according to Webster's Dictionary.
For the first syllable, pronounce "did" as you normally would. For the second syllable, pronounce "not" but without a vowel sound. This is a nasal sound followed by a stop with the tip of your tongue on your front teeth.
Run these sounds together as quickly as you can and you have "Didn't".
To answer your question, you should pronounce the both d's in "Didn't".
When two consonants make a distinct sound it is called a consonant digraph, but I don't think that's what you have here. There is a transition between the d and n in 'didn't', and that transition sound varies depending on dialect. The two letters are not forming a diagraph.
"Didn't" is, of course, a contraction of "did not". The "n't" part of this, or any other word (*can't, don't, won't etc) does have a slightly different pronunciation in British English to American English - although within both there are many more regional variations of dialect that might disprove any such rule.
If you listen to the audio examples provided by Cambridge, you will notice that the British pronunciation appears to have a vowel sound in there, making the transition between the d and n in "didn't" a little like those in the word hidden. As stated, this is just a different transition between the two letters and not actually the two letters forming a diagraph.
It is a nasally released stop, marked in IPA with a small subscript 'n' (unicode U+207F).
I doubt that any dialect has a glottal stop in that context.