Edge case: Ordering with dosage -o json does not know how to handle the existence of a previous ordered dosage.json?

[GittyGharial]

Dosage version: dosage 3.1.dev144+g48eb4ef

Use case: I use
dosage -o json
scripts/order-symlinks.py

to order downloaded strips for a certain comic, because the titles do not have any sequence embedded in them. That is, instead of ###-name.extension, they're just name.extension, which causes them to be jumbled. However, if a month later I want to download the latest strips and order them with reference to the previous ones, the second run of dosage does not seem to order the new strips properly. I've investigated the output json before and after and haven't exactly figured out what the problem is, but it seems to be at the boundary between the two session grabs.

That is:
February snatch lists B.jpg as the latest strip, with A.jpg as the prior strip before it.

The strip updated with 4 strips in between the next snatch (a monthly cron job).

March snatch updates the ordered output dosage.json from dosage -o json to list F.jpg as the latest strip, with prior strips E, D, C ordered correctly. However, where before the dosage.json entry for B.jpg listed A.jpg as the prior strip, now it lists E.jpg as the previous strip.

Possibly complicating matters, when I run order-symlinks.py on it it doesn't even add the new strips to the ordered folder -- not even with the garbled ordering.

If we are allowed to discuss specific sites I can attach a screenshot of a diff of the jsons for more clarity.