Money Order lost AFTER I received it from tenant and sent to bank

[Allan Smith]

Tenant did pay November rent, but my bank branch is far away, so I mailed them the money order. It's always worked in the past. It's been close to a month and the bank has not seen it, and it hasn't come back to me in the mail.

I requested tenant reissue that money order, we'll pay all fees. 

Tenant sent another payment (and I received it), but I'm not sure if it's the reissued money order or a new money order for december rent (like he's just moving on from Nov). He's not very communicative, but is somewhat trying to be a decent tenant.

What do I do? It seems I can't make him reissue the check, but i can't really evict him since there's a paper trail that I actually received his rent. 

I've already decided on what things will be changing for future months (NO MORE MONEY ORDERS IN THE MAIL, etc), but that doesn't help current situation. Additional background info: Tenant is late every month and needs several reminders to pay. Ultimately pays late fees - though before all this started I think he owed about half of a late fee.