Why doesn't automation work when I use "Send from organization" option?

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I have set up a workflow to Alert Someone when triggered. When I change the sender option to "Send from organization" I see my organization name. However, when I test it, I no longer receive a message (workflow doesn't run). If I change it back to "Send from Smartsheet automation" and test it again, it works just fine. The only change I am making is the send from option. Any ideas on why this isn't working?