Get Started - DropToSend.com

1) Requirements

Windows 10/11 or macOS 12+
Outlook for Windows/Mac or Gmail in your default browser
A local folder to drop files into (we create one during setup)
Optional: CSV/JSON metadata for multi-recipient addressing

2) Install

Download the installer: Get DropToSend
Run the installer and launch the app.
On first run, choose your email app:
- Outlook (creates a draft in Outlook)
- Gmail (opens a pre-filled Gmail draft in your browser)

You can switch later under Settings → Email App.

3) Your Drop Folder

During setup we create a default folder:

Windows

C:\DropToSend\sendbox

macOS

~/DropToSend/sendbox

Change this anytime in Settings → Folders.

4) Your First Drop (no metadata)

Drag a file (e.g., proposal.pdf) into your sendbox.
DropToSend opens a draft with the file attached.
Type your To, Subject, and Body, then send.

Prefer auto-send? Switch Settings → Send Mode to Auto-send.

5) Addressing with Metadata (single email)

Place a .meta (INI) or .meta.json file in the drop folder to prefill addressing. If both exist, .meta.json wins.

Example: INI

proposal.pdf
proposal.meta

to = alice@example.com; bob@example.com
cc = team@example.com
bcc =
subject = Q3 Proposal
body = Hi all—please see the attached proposal. Thanks!
send = draft   ; draft | send

Example: JSON (HTML body)

{
  "to": ["alice@example.com","bob@example.com"],
  "cc": ["team@example.com"],
  "subject": "Q3 Proposal",
  "bodyHtml": "<p>Hi all—please see the attached proposal.<br>Thanks!</p>",
  "send": "draft"
}

Use ; or , between addresses. send = send skips drafts and sends immediately.

6) Sending to Many: CSV recipient lists

Add a recipients.csv beside your files. We create one draft per row (or send, per your setting), attaching all dropped files.

recipients.csv

to,cc,bcc,subject,body,delaySeconds
sara@example.com,,,"Welcome","Hi Sara — welcome aboard!",0
ops@example.com,lead@example.com,,"Ops Update","See attached dashboard.",5

delaySeconds lets you throttle (e.g., 5 = wait 5 seconds between sends).
Works with Outlook or Gmail.

7) Remote Desktop (RDP) workflow

From a Remote session, save directly to the Local PC’s sendbox:

\\tsclient\C\DropToSend\sendbox

Make sure drive redirection is enabled in your RDP client.

8) Settings you’ll probably touch

Send Mode: Draft (safer) or Auto-send
Default To/Subject/Body: used when no metadata present
Throttling: delay between emails when using CSV

Folder Locations: change sendbox path
Email App: Outlook ↔ Gmail
Diagnostics: local logs toggle

9) Common Workflows

A) One PDF → one draft

Drop invoice.pdf. We create a draft with the file attached.

B) One PDF + `.meta`

Drop invoice.pdf + invoice.meta to prefill addressing/subject.

C) Many recipients (throttled)

Drop report.pdf + recipients.csv with delaySeconds=10 to pace delivery.

D) Mixed attachments

Drop multiple files—each generated draft includes all the dropped attachments.

10) File naming rules (quick sanity)

.meta/.meta.json in the folder applies to the whole drop.
If both exist, .meta.json wins.
If multiple .meta* files exist, we prefer one that matches your first attachment’s base name; otherwise use the single .meta* present.

11) Troubleshooting

No draft appears

Confirm you’re dropping into the correct path (Settings → Folders).
Outlook/Gmail must be installed/available; try switching app in Settings.

Gmail opens but message is empty

Browser blocked the pop-up. Allow pop-ups for DropToSend.

CSV created only one message

File must be named recipients.csv and have correct headers.
Save as UTF-8 with commas.

RDP path not found

Enable drive redirection in your RDP client.
Use: \\tsclient\C\DropToSend\sendbox

Auto-send isn’t sending

Set send = send in metadata or enable Auto-send in Settings.
Outlook may prompt the first time—allow the app to send.

12) Privacy & Security

Files never leave your machine unless you send them via Outlook/Gmail.
We don’t collect your attachments or recipients.
Optional logs stay local (toggle in Settings → Diagnostics).

13) Examples to copy-paste

Simple .meta

to = ops@example.com
subject = Monthly KPI Pack
body = Team—see attachments. Thanks!
send = draft

recipients.csv (throttled)

to,subject,body,delaySeconds
ann@example.com,"News","Hi Ann—attached.",3
ben@example.com,"News","Hi Ben—attached.",3
team@example.com,"News","Hi team—attached.",3

.meta.json with HTML

{
  "to": ["hr@example.com"],
  "cc": [],
  "subject": "Onboarding docs",
  "bodyHtml": "<p>Welcome! See the attached onboarding pack.</p>",
  "send": "send"
}