Sending contract for signatures, but only goes to wife even though I have two separate emails

We are sending a contract to a couple and ourselves for a project.

The couple's emails are similar, but different (ex jjsmith@example.com and jane.j.smith@differentprovider)

It has been sent three times. The first the husband did not receive it (we waited a week.) The second I checked the confirmation email immediately and it stated it went to Jane.j.smith, Jane Smith, and us for signature. The issue is when the husband tries to sign from his wife's computer, it of course wants to list him as Jane, but he never received the email even though I verified he was listed multiple times before I hit send. Please advise. We are all becoming increasingly frustrated. This is a time sensitive job and needs signatures before we can begin.

Running Windows 11 Pro, Adobe Acrobat 64 bit