My word processor soft-hyphenated condolences as condolenc-es. Does this look natural to the eyes of native speakers? I, a non-native speaker, think it should be condolen-ces.
If you were going solely by pronunciation, you would split the word condolen-ces. The word is split condolenc-es to keep the root word condolence as intact as possible.
Looking at similar words, Merriam-Webster suggests the line-breaking hyphenations chan-cel-lor and can-cel, but chanc-ing and danc-er.
The entire portion lence is a single syllable so it should technically not be split apart, however pluralizing the word causes the creation of an addistional syllable which cannot be expressed by s alone, so you'd have to add an extra e to express the proper syllable es so: