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How much trouble am I going to run into to change my straight steering column in my 68 XR7 to a tilt 69 column?
 

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If you have all the parts it is a straight bolt in. The tilt has a number of unique parts including the mounting bracket and rag joint. I switched my 68 Mustang to a tilt. It essentially the same as the 69. I have all the Mustang assembly manuals and that really helped with the wring and tilt mechanism placement.
 

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How much trouble am I going to run into to change my straight steering column in my 68 XR7 to a tilt 69 column?
ok good thanks. Now I have to paint the 69 column before I get started. The 69 column is a tilt/tilt away. I am planning on just using it as a tilt only.
 

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How much trouble am I going to run into to change my straight steering column in my 68 XR7 to a tilt 69 column?
The tilt-away interlock wiring harness is very different. You will need to obtain a 1968 tilt harness if you want the tilt-away function to work correctly.
 
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