2014 M7 Shifting Issue

The OP isn't saying the fluid is dark, but that the reservoir is actually black plastic, not the transluscent white. I've not seen a black one, but perhaps that was a running change - mine is a very early '14 with a white reservoir, and all my friends with C7s have the automatics. Not much to compare it to!

As for your actual shifting problem, it's possible the shifter needs realignment for better engage/disengage characteristics. Your dealer should be able to help there. When you check the fluid, check the color as well. If very dark (think coffee or tea) it should be replaced. Good fluid will be very nearly clear with just a hint of caramel color (think ginger ale). Again, the dealer can fix this. Yes, you should really be downshifting, as the upper gears aren't designed for very low speeds. As Fleet mentioned, the syncros can be a bit fussy. In most situations, I press the clutch in just before complete stop, and shift out of gear. Once stopped, I'll either keep it in neutral and watch for the cross light to go yellow, and slip into 1st just before I get green, or just keep the clutch pressed and immediately go into 1st while stopped at shorter intervals, such as stop signs, behind school buses, etc. I think Fleet is overall right, as on rare occassions I have to double clutch to get into first. My '14 Z51 M7 has 73xxx miles, and no major tranny issues.

Since you have a 2014, has the clutch fluid been changed? Had a 2014 and I recall the Owner’s Manual says do it every 2 years. The 2017 Grand Sport says every 3.

It is not easy to do per the Service Manual. To get at the slave cylinder bleed screw, need to remove the left exhaust pipe and CAT, then screws holding the sheet metal cover. Dealers charge >$150.

I have been using what is referred to as the Ranger Method at every oil change. You can google but will provide a brief description below. Not as good as a bleed but if you don’t Track or drag race good enough, IMO. I used for 6 years in my C6, 3 1/2 in my 2014 C7 and will on my Grand Sport when I change oil other than the first I did at 500 miles. Worth a try for the OP.

Ranger Method
1) buy a small container of DOT 4 (don’t use fluid from an open container)
2) use a turkey baster etc to remove all fluid from the clutch reservoir (suggest putting a large rag around the opening as the stuff eats paint)
3) fill with new fluid
4) pump clutch 30 times
5) repeat steps above 6 to 8 times (might as well use all the new fluid then discard as it is very hydroscopic)

You'll see the fluid will look new on the last few cycles. You’ll also get a great left leg exercise!