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Is your Outback a stick or Automatic?
There is a special holder (tool) for the crankshaft front pulley and is required for stick and automatic, but if it is an automatic you can get away without the tool by accessing the torque converter bolts at the rear of the motor...the access opening is under the air cleaner and is covered with a black rubber plug (see the diagram I am attaching) once you take the cover off, rotate the engine with the 7/8 socket on the crank pulley (clockwise) , when you see a torque converter bolt at that rear opening, you can fit a screw driver between the bolt and trans case enough to hole the engine from turning as you loosen the crank bolt, you may need a helper to hold jam that big screw driver or break the bolt loose, then do the same thing to tighten the bolt after you are done. If the vehicle is a stick, you will need the tool, here is the part number and a pic is attached.
Crankshaft pulley wrench..#499977000