Automated emails not sending attachtments?

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I have a simple automation set up where if Cell 1 has any value in it, It will send out an email to the requestor. Sometimes we have to include attachments but it doesn't always send. I already have it set up to send the information needed and I made sure attachments were checked as well. I also told all the admins "add the attachment before adding any text to Cell 1". Is there something I am missing or do we have to save the sheet when we add the attachment then add text to Cell 1 so the workflow runs with the attachment? Is there a way around this by either creating an few automations and or using helper columns as I can not have the automation based on if an attachment is added as it is only sometimes.