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Upon rewatching the episode of DS9 where Sisko and Garak bring the Romulans into the Dominion war, I realized that there are a few episodes and mentioned instances where either the Obsidian Order or Starfleet (and section 31) pull one over on the Tal Shiar.

I can only vaguely recall one instance of the Romulans debatably pulling anything tricky (the time they tricked a defector into luring the Enterprise into the neutral zone), and I'm not actually sure if that was the Tal Shiar per se. Even then, Picard took precautions when moving the Enterprise in.

Obviously the Tal Shiar are known for being tricky spies, but are there any Star Trek episodes where the Tal Shiar, or even just the Romulans, pull one over on any other race and get away with it?

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  • The Romulans do come off as rather foolish in DS9... perhaps because the Cardassians and (later) the Klingons were considered more important (not to mention the Dominion).
    – Kevin
    Apr 1, 2016 at 5:15
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    They made the Federation give up on developing cloaking devices. While it wasn't exactly a trick, it certainly did have a huge impact.
    – Zommuter
    Apr 1, 2016 at 12:00
  • True, but I was mostly thinking about how they're oft portrayed as these master spies, but i couldn't remember a case in the episodes where they lived up to that legacy.
    – Cone_of_Silence
    Apr 1, 2016 at 12:52

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YES

In "Data's Day" the Romulans get over big time on the Federation by planting a spy disguised as Vulcan ambassador and successfully retrieving her.

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  • Excellent example! I always thought this was quite a chilling episode. The equally excellent Outer Limits episode "Quality of Mercy" reminds me of this TNG one. :-)
    – Praxis
    Apr 1, 2016 at 2:30
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    You know, I remember some of the scenes where data narrates, but literally don't recall the plot.
    – Cone_of_Silence
    Apr 1, 2016 at 4:38
  • One of my favorite episodes
    – user126198
    Apr 16, 2020 at 16:03

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