Just published a new blog on our website on proving email receipt in forensic investigations. You can read it here:
I would be interested to hear what other strategies you use in similar scenarios. 
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I came across a brief discussion on LinkedIn (in Italian) regarding the efficacy of the filing mailbox approach. One of the participants stated that the approach didn’t make much sense to them as there was no proof of delivery to the recipient.
I agree, and I attempted to make that clear in the article. That said, in some cases, the sender’s good faith effort to communicate by the required method and deadline can satisfy their legal obligations [1].
Additionally, if the sender and recipient exchanged a large number of emails throughout their relationship, and if the recipient claims not to have received only a few key emails that the sender can prove they had sent, what does that say to the finder of fact?
Some examples that come to mind: contract formation disputes, legal notice requirements, employment disputes, insurance claims, statute of limitations issues, intellectual property disputes, etc. ↩︎