Three options for sending sensitive documents: fax, email, encrypted file sharing. Each has specific strengths.
Use fax when:
- The recipient explicitly requires fax (healthcare, government, certain legal)
- You need a time-stamped legal record of transmission
- The document is signed and you need confirmed receipt
- HIPAA compliance is required (fax is grandfathered)
Use email when:
- The document is low-to-medium sensitivity
- Recipient prefers email
- You need a permanent searchable record
- You're sending to a known, trusted recipient
Use encrypted file sharing when:
- The document is highly sensitive (medical records, legal contracts, financial)
- File size exceeds 25MB (most email limits)
- You want recipient-side access tracking
- You need to set expiration dates
Encrypted file sharing services worth using:
- Tresorit Send — zero-knowledge encryption, free for 5GB files
- Firefox Send (discontinued — RIP)
- WeTransfer — free 2GB transfers, not encrypted by default
- Dropbox Transfer — encrypted, $11.99/month
- Sync.com Send — zero-knowledge encryption, free
- Apple iCloud Mail Drop — free 5GB, encrypted
Email encryption (if you must use email):
- ProtonMail — end-to-end encrypted by default
- Tutanota — similar, encrypted by default
- Gmail confidential mode — adds expiration + screenshot protection (not true encryption)
- PGP keys — old-school but bulletproof if both sides set up
Comparison table:
| Need | Fax | Email | Encrypted Share |
|---|---|---|---|
| HIPAA-required | ✓ | ✗ | Sometimes |
| Legal proof of delivery | ✓ | Weak | ✓ |
| Time-stamped | ✓ | Weak | ✓ |
| Large files (>25MB) | ✗ | ✗ | ✓ |
| Encryption | Carrier-dependent | Server-dependent | ✓ |
| Cost | Free (some) | Free | Free-mid |
| Speed | 1-3 min | Seconds | Seconds |
When NOT to use fax:
- Color documents (most fax is black-and-white)
- Photos requiring detail
- Documents over 50 pages
- International (expensive per-page)
The lawyer framework:
1. Has the recipient specified a delivery method? Use that.
2. Does the document require signed receipt? Use fax or registered mail.
3. Is it under 25MB and to a trusted recipient? Use email.
4. Is it sensitive + large? Use encrypted file sharing.
5. Is it a digital signature contract? Use DocuSign or HelloSign (also handles legal validation).
For occasional fax needs, Wikishopline Fax is free for the first 3 pages monthly.