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'failed to fail' is correct and usable in written English
You can use it when referring to something that was expected to fail but ultimately was successful. Example: Despite the difficult odds, the team failed to fail and achieved an unexpected victory.
Exact(6)
In its efforts to weaken civil-rights legislation, the Administration had succeeded in failing, but this time it failed to fail.
Above all, viols have failed to fail because the music written for them commands attention.
"The Hepatitis Bathtub" is nominally a story about a band that somehow failed to fail, but it is also an estimable work of anthropology, criminology, and, above all, pharmacology.
Twitter failed to fail, and I am a happy user today.
I'd say the email is tempting fate a little, but I've called Twitter on that same issue before and they failed to fail.
In 2007 they called the upstart Hulu joint venture Clown Co. as a private joke about the messy start to that unlikely company (I was right there mocking Hulu with them, but later gave them their due when they failed to fail).
Similar(54)
The play, however, fails to fail, which leads to a slew of unpredictable consequences.
Remember regulators are designed, if they fail, to fail open, causing a lot of air to come out.
If you fail to fail to mail the letter in well before the 25th, you'll be held accountable for the next month's worth of purchases.
Has a work failed if it fails to go viral?
Why it failed: You failed to fund a funding conference?
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Since I tried Ludwig back in 2017, I have been constantly using it in both editing and translation. Ever since, I suggest it to my translators at ProSciEditing.

Justyna Jupowicz-Kozak
CEO of Professional Science Editing for Scientists @ prosciediting.com