Missing Orders

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We currently have our notifications set to send all new orders through to 3 different email address. Of the 3 email addresses 1 seems to receive ALL the orders, while the other 2 seem to be intermittent and will only receive approximately 75% of the orders, but then randomly over the next 1-2 weeks the orders that are missing will randomly all appear. I'm not sure if this is a Shopify issue, or if it's an Outlook issue. Has anyone else experience this?