The phrase "again, although" is correct and usable in written English.
It can be used to introduce a contrasting idea or to acknowledge a previous point while presenting a new perspective.
Example: "Again, although we faced many challenges, we managed to complete the project on time."
Alternatives: "once more, even though" or "yet again, despite".
Exact(60)
He'd never called again, although she almost wished he had.
You can say that again, although you don't have to.
Geography was in play again, although now considerably more loaded.
Then in 1982, he started classes again, although he told no one about his academic life.
Later, she watched it again, although by this time she was an actor.
He never sees his father again, although his father lives another thirty years.
This time, Kasich won again, although it was a closer call.
Soon, however, problems began picking up again, although at a lower volume than before.
They came back to level again, although with the help of a forward-looking pass.
He said he is is too frail to return again, although he would like to.
Miller never talked any sort of crap to Jordan again (although he did fight him).
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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