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Instead of "Trials and Tribbleations"

A sequel to The Doomsday Machine might have worked…say they find one in the Gamma Quadrant. But doing a sequel to one of the more lighthearted episode was a much better choice. I think A Piece of the Action would have worked well too.
 
How about the Doomsday Machine comes through the Alpha Quadrant during the Dominion War. The Federation knows what you need is a starship on self-destruct heading into it. But it starts chewing up Cardassian planets and Jem Hadar ships. Will the Federation share what they know to help the Dominion defeat it? Will the Dominion believe them at least long enough to try? Is this the new Generation 2 Doomsday Machine that cannot be defeated so easily?
 
How about the Doomsday Machine comes through the Alpha Quadrant during the Dominion War. The Federation knows what you need is a starship on self-destruct heading into it. But it starts chewing up Cardassian planets and Jem Hadar ships. Will the Federation share what they know to help the Dominion defeat it? Will the Dominion believe them at least long enough to try? Is this the new Generation 2 Doomsday Machine that cannot be defeated so easily?
That could have been a two episode story, before season 7.
 
Suppose DS9 had chosen to use "A Piece of the Action" or "Charlie X" for its TOS crossover. (For that matter, any other TOS episode, really.)

What would the DS9 characters do in these episodes? Why would an episode not be a good crossover choice?

I think they wanted to do a comedy as that would allow a lot more references. But they did do a sequel to all of the Klingon episodes after all with Dax's revenge plot.
 
Okay. ‘The City on the Edge of Forever’. That could be complicated, but Sisco and Odo and Bashir dive into the guardian to bring The guys home while making sure that Eidith Keeler gets hit by the truck.
Would have be great for Sisko and Odo to be driving the truck after somehow accidentally incapacitating the driver.
 
Okay. ‘The City on the Edge of Forever’. That could be complicated, but Sisco and Odo and Bashir dive into the guardian to bring The guys home while making sure that Eidith Keeler gets hit by the truck.

Odo: "We have to make sure Edith Keeler gets hit by the truck, without being seen by Kirk or Spock. The consequences of that could be disastrous."
Spock: "Excuse me. Yes, you with the hat."
Odo: "Who, me?"
Spock: "Yes. Be a pal and hand me some stone knives and bearskins out of that toolbox."
 
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