Yes.
In the same way nature evolves some physical characteristic in an species, it can "involute" (retrieve the characteristic) and change to a previous state. For example, the blind fish that live in deep lakes inside caves (cavefishes). They once had eyes, but the eyes rendered useless in the new environment, so Mother Nature took them away. Here is the link:
https://www.leisurepro.com/blog/explore-the-blue/blind-fish-species/
In the same way, dolphins and whales still have pelvic bones. They evolved from land-dwelling ancestors more than 40 million years ago, and although they have legs no more, they preserve vestigial hips.
So the short answer is "Yes": If the ecosystem where your digitigrade limbs creature lives changes enough, Nature will make your creature change in order to adapt to the new conditions, and if the new "best fit" characteristic involves plantigrade limgs, then so be it.
So... the answer to your second question: What changes in my ecosystem can make a digitigrade creature evolve into a plantigrade creature?
Let us start reviewing very briefly each one:
Digitigrade: They can execute quicker and faster movements.
Plantigrade: Generally can carry a heavier load, have a greater surface area, but are slower.
I can think right now of 3 changes in the ecosystem that could lead to such a change:
1) Shortage in the sources of food, so the animal needed to have more fat reserves, therefore started to weight more, and the feet needed to tradeoff their dexterity versus carry their own weight.
2) Predator extintion: If the animal has no need of running away faster or being more agile than the extinct predator, then the need of the agile feet will eventually dissappear.
3) Prey change: The prey once hunted dissappeard from the ecosystem, and were replaced by others more slow and easy to hunt (but of course with a higher reproduction ratio, to compensate that). So your animal needed its agility no more.