Documents & E-Signatures

Uploading Documents

The two upload intents — Store a file in a folder, or Send it for signature — plus accepted file types, size limits, and how plan document limits are counted.

Uploading Documents

Uploading in BookYourPTO has two distinct intents, and choosing the right one matters because they behave completely differently. The upload page has a mode switch at the top, and a persistent banner always shows which mode is active.

Why the banner exists. People kept uploading a contract in Store mode when they meant to send it for signature (and vice-versa). The always-on banner makes the active mode unmistakable before you commit a file.

Mode 1 — Store ("Upload to folder")

Use Store when you just need to file a document — a passport scan, a signed PDF you received elsewhere, a tax form. It goes straight into a folder. No signature is requested.

Accepted files

Property	Value
File types	PDF, DOC, DOCX, PNG, JPG / JPEG
Max size	25 MB
Type check	Magic-byte sniffing — a file's real contents must match its extension

Fields

Field	Required	Notes
Category	Yes	One of the 13 built-in categories
Folder	Optional	A custom folder within the drawer
Expiry date	Optional	Triggers expiry reminders — see below
Tags	Optional	Free-text labels for search and grouping

Expiry reminders

If you set an expiry date on a stored document (passport, visa, certificate), BookYourPTO sends reminders at 60, 30, 7, and 0 days before it expires. The reminders go to the document owner (always) plus a role-based audience (admins / execs / HR). This is separate from signing-deadline reminders covered in E-signatures.

Mode 2 — Sign ("Send for signature")

Use Sign when a document needs one or more people to sign it. This launches the recipient + field-placement flow described in detail under E-signatures.

Accepted files

Property	Value
File type	PDF only
Max size	10 MB
Min size	1 KB (rejects empty/zero-byte files)

Why PDF-only for signing. Signature fields are placed at exact page coordinates and a certificate page is appended to the finished file. That only works reliably on a fixed-layout format — so signing accepts PDF only, while plain filing accepts the broader Office/image set.

Plan document limits

Documents count against your plan's allowance. The counting rule is what trips people up:

A single upload counts as 1 (the file) + 1 per recipient (each signer assignment).
A bulk send counts 2 × recipients.

Plan	Document limit
Free	50
Pro	50
Business	100
Enterprise	Unlimited

Worked example. Sending one contract to 3 people for signature consumes 4 of your allowance (1 file + 3 assignments), not 1. A 3-recipient bulk send consumes 6.

Security at upload

Magic-byte sniffing inspects the actual bytes of the file, so a .exe renamed to .pdf (a spoofed type) is rejected even though the extension looks valid.
Once stored, the file is encrypted at rest (AES-256-GCM) and a SHA-256 checksum is recorded — see Overview.

Roles & permissions

Role	Upload to own drawer	Upload to others' drawers	Send for signature
EMPLOYEE	Yes	No	To self / as allowed
DEPARTMENT_HEAD	Yes	Reports / department	Yes (department scope)
ADMINISTRATOR	Yes	Anyone	Anyone
EXECUTIVE	Yes	Anyone	Anyone

Troubleshooting

Error / symptom	Cause	Fix
File ended up un-signed when you wanted signatures (or the reverse)	Wrong upload mode	Use the mode switch; confirm against the persistent banner before uploading
"Document limit reached"	Allowance hit — recipients count, bulk send counts double	Remove old documents, reduce recipients, or upgrade your plan
File rejected on upload	Type/size out of bounds	Store: PDF/DOC/DOCX/PNG/JPG ≤ 25 MB. Sign: PDF ≤ 10 MB (≥ 1 KB)
"Invalid file type" despite a `.pdf` name	Spoofed type — bytes don't match the extension	Re-export a genuine PDF and upload again
Expiry reminders never arrive	No expiry date was set, or document was sent for signature (not stored)	Add an expiry date in Store mode

Overview

How the BookYourPTO document hub works — the personal filing cabinet, built-in and custom folders, the Company Library, and how files are encrypted and protected at rest.

E-Signatures

The full send-for-signature flow — recipients, parallel vs sequential signing, drag-and-drop field placement, the signer experience, and how a document is completed and certified.