The first problem I see is that the Indenter does not start out touching the bone.

Bonded Contact is on the tip so that the Static Structural model can start. If you don’t have initial contact and have a force driving the indenter, there is no solution if there is no initial contact.

After I delete the Bonded Contact, I ran a Contact Tool to get the Initial Contact Status on the Frictional contact.

You can see there is a 25 micron gap.

A quick and easy fix for that is to use “Adjust to Touch” in the contact details and it will close that gap automatically by moving the contact surface by that amount. But it might not move it along the Z axis, it finds the smallest distance and moves it in that direction.

Mechanical issued a warning.

The solver issued a warning.

*** WARNING ***                         CP =       7.656   TIME= 09:01:01
 Meshes made up of 10 percent or more of SOLID185 tetrahedra are not recommended.

You should consider following that advice, however the model will take longer to solve.

You have 4 steps, but no load is applied in Step 1.  I reconfigured the steps like this:

Finally, under Analysis Settings, you must have Large Deflection turned on.

It is solving now with those changes and I will report back later.