Brake Shoes alignment

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I am assuming the wheel cylinders move freely
Order away
If you are just watching the shoes move under pressure
And one moves before the other
That is okay
The misalignment is usually from an applied E brake
 
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So I installed the new cylinders. Everything looks in place but the brakes shoes don't move when I step on the brake pedals, additionally the brake pedals felt a little soft so I suspected there was some air in the brake lines and I needed to bleed them.
I had my friend help me pump the brake pedals a couple times, and as suspected air bubbles came out the bleeder, and then the primary brake shoe moved a little bit.
This is where I think I messed up... I told my friend to step on the brakes again so I can bleed it one more time. The brake shoes came out of the wheel cylinder and tore the rubber seal on the cylinder. How do I prevent the brake shoes from coming out? Was the drum supposed to be on to prevent the brake shoes from over extending?
See the pictures below (first one is the assembly with the new cylinders, second one is the primary shoe coming out and ripping the wheel cylinder. As you can see only the primary shoe side ripped because only the primary shoe seem to be moving when I step on the brakes)
 

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So I installed the new cylinders. Everything looks in place but the brakes shoes don't move when I step on the brake pedals, additionally the brake pedals felt a little soft so I suspected there was some air in the brake lines and I needed to bleed them.
I had my friend help me pump the brake pedals a couple times, and as suspected air bubbles came out the bleeder, and then the primary brake shoe moved a little bit.
This is where I think I messed up... I told my friend to step on the brakes again so I can bleed it one more time. The brake shoes came out of the wheel cylinder and tore the rubber seal on the cylinder. How do I prevent the brake shoes from coming out? Was the drum supposed to be on to prevent the brake shoes from over extending?
See the pictures below (first one is the assembly with the new cylinders, second one is the primary shoe coming out and ripping the wheel cylinder. As you can see only the primary shoe side ripped because only the primary shoe seem to be moving when I step on the brakes)
Sorry for replying to myself.. I put the drums on and bled the brakes that way, I think that prevented the pistons from over traveling. I believe my rear brakes work now (based on seeing the drum move when I press on the brake pedals). Additionally, the brake pedals are firm again.

Now the problem is that the parking brake won't hold my car in place. I have already installed new parking brake cables. When I pull on the handle on the parking brake assembly, there is no resistance and I could easily pull it all the way up. Is this a symptom of my rear brake shoes needing adjustment? If so, how does the "self adjuster" work, or should I manually expand the self adjuster through the hole on the backing plate?
 
Wow, did that post bring back memories,
First, you need to address an issue you created when the plunger (the round thingy inside the wheel cylinder) over extended, you can get a rebuild kit that replaces the plungers and rubber seals, likely all you need is to replace the rubber part, if it's torn brake dust and junk will ruin the cylinder walls in short order, next put the drum on and rotate the axle/drum while adjusting the shoes, this is done by rotating the adjustment wheel through the slot you mentioned, do both sides, until you feel the shoes dragging on the drum, I generally put the wheels on at this point then drive some place I can back-up safely and press the pedal several times firmly and they should adjust themselves equally.
Get that done and see if the E brake functions better.I
Now this assumes no air in the system.
 
Wow, did that post bring back memories,
First, you need to address an issue you created when the plunger (the round thingy inside the wheel cylinder) over extended, you can get a rebuild kit that replaces the plungers and rubber seals, likely all you need is to replace the rubber part, if it's torn brake dust and junk will ruin the cylinder walls in short order, next put the drum on and rotate the axle/drum while adjusting the shoes, this is done by rotating the adjustment wheel through the slot you mentioned, do both sides, until you feel the shoes dragging on the drum, I generally put the wheels on at this point then drive some place I can back-up safely and press the pedal several times firmly and they should adjust themselves equally.
Get that done and see if the E brake functions better.I
Now this assumes no air in the system.

Wow, did that post bring back memories,
First, you need to address an issue you created when the plunger (the round thingy inside the wheel cylinder) over extended, you can get a rebuild kit that replaces the plungers and rubber seals, likely all you need is to replace the rubber part, if it's torn brake dust and junk will ruin the cylinder walls in short order, next put the drum on and rotate the axle/drum while adjusting the shoes, this is done by rotating the adjustment wheel through the slot you mentioned, do both sides, until you feel the shoes dragging on the drum, I generally put the wheels on at this point then drive some place I can back-up safely and press the pedal several times firmly and they should adjust themselves equally.
Get that done and see if the E brake functions better.I
Now this assumes no air in the system.
Thank you!
Luckily I bought an extra wheel cylinder, so I just went ahead and installed the new one when the other one over-extended.
I will rotate the adjustment wheel and try backing it up to see if that makes a difference!
 
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Remember you have to push the brake peddle firmly several times, like alot, the self adjuster only turns the wheel a click or two at a time.
I followed your instructions to no avail. On both sides, I made the self-adjusters expand until the drums are kind of dragging on the shoes when I spin it (around one wheel rotation when I try to spin it real hard). After putting on the wheels, I went to an empty parking lot and pushed on the brake pedals hard many times while going in reverse.

The E brake is still very lose and is not holding the car in place. What do you recommend doing next?
 
Not on an 89 according to my book. Maybe older models, I know there is a pawl that releases the tension on the spring but I wouldn't mess with that just yet.
I think I figured out what the problem is (see my other thread https://www.stangnet.com/mustang-forums/threads/parking-brake-not-engaging.921832/#post-9328090)
The pawl is sitting on the last tooth of the gear on the e-brake assembly, therefore giving too much slack to the e-brake cable which is attached to the wheel that is connected to the gear on the e-brake assembly. I wonder if I can remove the e brake cable from the e-brake assembly and readjust the positioning of the gear, so that when the e-brake is disengaged the pawl sits on a lower tooth