It appears reinstalling open-vm-tools after performing an "apt-get autoclean" followed by "apt-get autoremove" cleared the issue.
I'm guessing open-vm-tools got confused because of multiple 4.x kernels or tried to compile against the wrong headers. ********** # apt-get autoremove Reading package lists... Done Building dependency tree Reading state information... Done The following packages will be REMOVED: linux-compiler-gcc-4.8-x86 linux-headers-3.16.0-4-amd64 linux-headers-3.16.0-4-common linux-image-3.16.0-4-amd64 linux-kbuild-3.16 0 upgraded, 0 newly installed, 5 to remove and 0 not upgraded. After this operation, 189 MB disk space will be freed. Do you want to continue? [Y/n] Y (Reading database ... 199260 files and directories currently installed.) Removing linux-headers-3.16.0-4-amd64 (3.16.7-ckt11-1+deb8u4) ... Removing linux-compiler-gcc-4.8-x86 (3.16.7-ckt11-1+deb8u4) ... Removing linux-headers-3.16.0-4-common (3.16.7-ckt11-1+deb8u4) ... Removing linux-image-3.16.0-4-amd64 (3.16.7-ckt11-1+deb8u4) ... /etc/kernel/prerm.d/dkms: dkms: removing: open-vm-tools 9.10.2 (3.16.0-4-amd64) (x86_64) /etc/kernel/postrm.d/initramfs-tools: update-initramfs: Deleting /boot/initrd.img-3.16.0-4-amd64 /etc/kernel/postrm.d/zz-update-grub: Generating grub configuration file ... Found background image: /usr/share/images/desktop-base/desktop-grub.png Found linux image: /boot/vmlinuz-4.2.0-1-amd64 Found initrd image: /boot/initrd.img-4.2.0-1-amd64 Found linux image: /boot/vmlinuz-4.1.0-2-amd64 Found initrd image: /boot/initrd.img-4.1.0-2-amd64 Found memtest86+ image: /boot/memtest86+.bin Found memtest86+ multiboot image: /boot/memtest86+_multiboot.bin done Removing linux-kbuild-3.16 (3.16-3) ... # ls /boot/ config-4.1.0-2-amd64 initrd.img-4.2.0-1-amd64 System.map-4.2.0-1-amd64 config-4.2.0-1-amd64 memtest86+.bin vmlinuz-4.1.0-2-amd64 grub memtest86+_multiboot.bin vmlinuz-4.2.0-1-amd64 initrd.img-4.1.0-2-amd64 System.map-4.1.0-2-amd64 # sudo rm /boot/*4.1.0* Generating grub configuration file ... Found background image: /usr/share/images/desktop-base/desktop-grub.png Found linux image: /boot/vmlinuz-4.2.0-1-amd64 Found initrd image: /boot/initrd.img-4.2.0-1-amd64 Found memtest86+ image: /boot/memtest86+.bin Found memtest86+ multiboot image: /boot/memtest86+_multiboot.bin done # apt-get install --reinstall open-vm-tools Reading package lists... Done Building dependency tree Reading state information... Done 0 upgraded, 0 newly installed, 1 reinstalled, 0 to remove and 0 not upgraded. Need to get 0 B/514 kB of archives. After this operation, 0 B of additional disk space will be used. (Reading database ... 184678 files and directories currently installed.) Preparing to unpack .../open-vm-tools_2%3a9.10.2-2822639-3+b1_amd64.deb ... Unpacking open-vm-tools (2:9.10.2-2822639-3+b1) over (2:9.10.2-2822639-3+b1) ... Processing triggers for systemd (226-3) ... Processing triggers for man-db (2.7.3-1) ... Setting up open-vm-tools (2:9.10.2-2822639-3+b1) ... Processing triggers for libc-bin (2.19-22) ...
