Will rubber expansion plugs damage threaded fittings?

I closed my pool about 4 weeks ago trying the air-lock method. I used a blow-through expansion valve in my skimmer. Pretty sure I was successful as I heard / saw nothing that would indicate a leaky seal.

Today I decided to check the skimmer and it was full of water - the expansion plug had popped out. This could be a big problem for me as I'm in a very cold winter zone.

My two questions are, do I want to fit the expansion in the unthreaded or threaded area of the skimmer drain pipe? As I recall I fitted it down into the unthreaded portion. Secondly how tight should I tighten the wing nut, I want it secure but concerned about damaging threads especially in skimmer. Thanks.
 
You have to be a little more specific on why and how you "air locked" the skimmers? Most skimmers lines are cleared with a blower (after water is lowered slightly below the skimmer) and then either a Gizzmo or black winter plug, or even a threaded plug is used. The plugs can be either inside the threads or outside the threads. You will only need to turn the wing nut just enough so no air bubble are coming out, but this is only when closing under water. If your skimmer was empty, then you should be using a Gizzmo with Teflon Tape.

Can you please describe how you cleared the skimmer lines and what you did before and during the process. Did you lower the water below the skimmers? What kind of cover do you have? Did your area receive any rain since the closing? Your plug may have popped out just because of incorrect installation as well. Do you have a main drain, and is it separate from the skimmer or all in one? Pictures of even the skimmer area would be helpful as well.

Also, can you please upload pictures of the equipment pad?
 
Catanzaro, here is the long version. I have a mesh safety cover and yes we've had a lot of rain lately.

Photos: https://imgur.com/a/zu6jYyg

Photo 1 – pool view with connected spa
Photo 2 – tiled skimmer on left, pool drain in deep end
Photo 3 – Skimmer basket. Pipe closest to pool connects to main drain. Other pipe goes to pump. Photo shows how pool co. closed it last winter, with foam rope and threaded plugs (not air locked).
Photo 4 – Equipment pad. Red valves from L to R: in from spa drain, in from pool skimmer, out to spa jets, out to pool jets (not in photo).

How I closed:
  1. Drained pump & filter.
  2. Lowered pool water below jets, skimmer and spa overflow.
  3. Closed spa by emptying all water. From equipment pad, unscrewed the Spa Out and Spa In unions and blew out the jets and the drain using a shop vac. Threaded plugs inserted into spa jets, rubber expansion plug in spa drain. At pad, closed red valves and reconnected the Spa in/out unions.
  4. Closed pool jets. Unscrewed Pool Out union at pad and blew out using shop vac. Inserted threaded plugs into the jets. At pad, closed red valve and re-connected Pool Out union.
  5. Closed skimmer line. I did this by connecting a compressor to the pump basket, with only the Pool In valve open. A helped vacuumed up water in the skimmer. Closed the Pool In valve then plugged skimmer pipe with threaded plug.
  6. Closed main drain (air-lock). I inserted a #8 blow through plug (https://www.amazon.com/Technical-Products-Winter-Plug-Valve/dp/B004UHCRFA) into the skimmer drain pipe, into the non-threaded part. I used a compressor to blow at around 20 PSI for about 3 minutes. Lots of bubbles the whole time. Stopped and capped the blow through valve. Dropped pieces of rope and a loose Gizzmo into the empty skimmer basket and figured I had achieved an air-locked closing.
  7. Refill spa and raise pool level to about 18" below deck.
Since the weather will get worse soon, I think I’ll try again later today by inserting the plug into the threaded part of the pipe and tighten very firmly. But I would definitely appreciate any feedback because I was hoping to leave the drain air-locked permanently and I definitely don't want to lower the water and close again in Dec.
 
Plastered:

The water filled up because of rain. Why your plug popped out is a mystery. The # 8 should fid snug inside the threads against the flush part. What you could do is clear the main drain line again with the # 8 plug with an air compressor. The plug should sit inside the threads and you should hand tighten (not too much as you do not want to break the wing nut) just enough where if you pull on the valve, the plug does not come out Then keep an eye on it to make sure it does not pop out. If it does then you will have to do what the pool company has done in the past.

- - - Updated - - -

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The plugs are less expensive on PoolWeb (like 25% of the cost). Free shipping over $50. Thanks!
 
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