Color management with linked files sometimes defaults

we've noticed that Illustrator sometimes does not honor linked or embedded color profiles as expected. The  .ai files that we use include a specific custom color profile that has a wider color gamut, Illustrator appears to sometimes ignore this profile and instead defaults to the working space. This can lead to noticeable color shifts when we print.
We've found that manually assigning the intended color profile for these specific instances within Illustrator (via Edit > Assign Profile) can correct the appearance. This seems to only happen to specific files, others come out as expected, it also appears to be an issue that started recently, about a month ago. The color management in both illustrator and photoshop are set to preserve embedded profiles.

We save a file as a tiff in photoshop under our custom color profile. We drag it into a blank canvas in illustrator, its not a linked file. We copy over a label that was made in indesign, then save as an .ai file. We did noticed illustrator working space was set to Web Coated Swop v2 but our understanding that wouldnt be an issue since the files being linked have their own color profile and its set to preserve the embedded profile.