There's a mismatch between how the Startup Manager and Grub2 work.

While the Startup Manager counts the expanded number of menuentry
clauses in /boot/grub/grub.cfg, Grub2 counts the number of those in the
compressed menu displayed at startup. Consequently, all older kernels
are counted as one only.

This implies that an older kernel cannot be selected automatically at
startup which does not make sense.

Thus, this seems to be a bug in Grub2.

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https://bugs.launchpad.net/bugs/775292

Title:
  Chosen boot options do not work for Grub 1.99

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