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I have enable "Speech" on the MacOS system and run this command and hear the output:

say "Hello there"

But if I try to run following command:

say -o "Hello, this is not working"

The terminal seems like is doing something and hangs but creates the file

enter image description here

The file is there but I can play it. I open the file on iTunes but doesn't play any sound.

Any of you knows what I'm doing wrong of if there is a trick to make this work?

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With say -o, you need to specify a filename to save the audio under. The command format is say -o filename.aiff "Thing to say". You only specified one thing after -o, so the command interpreted that ("Hello, this is not working") as the filename to save under, and since there was nothing after that... it didn't actually say anything.

Solution:

say -o This-is-working.aiff "This is working"

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