Hey Streamer,
Okay, I just attached the BIABacus for my second to last brew... It was a Vienna Lager where I had to make adjustments to the OG, post boil... You can see where I recorded what gravity was measured, and then after doing the math and adding water and remeasuring, see what gravity that I ended up with. Follow down that entire column to the bottom - check out what each cell does.
For certain I measure GIB (Gravity Into Boil). I get a cup of wort at the end of the mash...and cool it down, and then use my hydrometer to get a reading. That process probably takes 30 minutes or so, and I add this wort back into the boil with an hour or so to go (it's okay because the boil will sterilize it...don't forget though). Yes, measuring the GIB would tell us if we are going south...provided the instrument you are measuring with is accurate.
One measurement that I don't normally get is the VFO (Volume at Flame Out, before you've chilled the wort if you chill like I do). Usually working too hard with the immersion chiller...and stirring the wort to cool quick. I do measure after the wort is chilled and then adjust the VFO until the VAW matches what I actually have.
I would recommend NOT making adjustments such as adding DME, etc., until you know what's going on... I honestly think it is likely there are some measurement issues causing this. Not sure exactly where... In the military when we were "zeroing" our weapons we had to "tighten our shot group up" - where rounds being fired were all hitting in about the same point (off target is okay, provided all hitting in the same basic point). Only then could we "adjust" the sights to allow rounds to hit the bulls-eye. Does this make sense (or am I confusing the heck out of you...?)

Get the process down well first, document things, make sure your measurements are as good as you can get them. Adjust later, after you are getting "consistent" results.
Personal Example:
One note - my Bayou Classic boil kettle came with pre-engraved inside the pot. Cool, right? Exactly what I wanted... Only when I had some issues back at the start on the volume, and when I checked the brew pot (by pouring 1/2 gallon big measuring cups into the pot) discovered my markings were off. By up to 0.4 gallons, when almost full. I have to have a "cheat sheet" that gives me the correct info. (By the way, I confirmed the 1/2 gallon by using smaller measuring cups to pour into it, etc.). Anyhow, for certain you should check all instruments you use to measure (including volumes), and get a nice new hydrometer to also use with taking measurements...
Conclusion:
There is a logical explanation. I don't know what it is yet, but my best guess is a measurement (or multiple) might be inaccurate... So don't worry about it...just work to be accurate and document well, and it will likely jump out at you at some point. Pretty sure that will happen.
You do not have the required permissions to view the files attached to this post.