Every day the first time I call this flow - the flow fails. I believe this is related to the first authentication of the day because subsequent attempts are succesful.
The problem is I need to retrigger the flow in the event of an error.
What happens here if I check both of these boxes? Will it execute once or twice?
It looks like your topic is missing some important information. Could you provide the following if applicable.
Hi @Nicholas_Mitchell ,
Welcome to the community! 
So, the “Execute Once” toggle is for nodes that are receiving more than one item as input.
For example, if you’re getting a list of 10 items and then filtering them for a certain conditional, activating “Execute Once” on the Filter Node will make it run just for the 1st item.
If, at the same time, you activate the “Retry On Fail” toggle with 2 tries, and there is an error, the node will run twice but only for the 1st item.
If your input is already only one item, “Execute Once” won’t actually have a visible outcome.
So in this case the short answer is the node will run twice 
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