# SecureMailMerge

> Advanced mail merge plugin for Microsoft Outlook 365

SecureMailMerge is a mail merge add-in for Microsoft Outlook that enables personalized bulk email campaigns with advanced features like individual attachments, CC/BCC per recipient, scheduled sending, and more. It processes all data locally on your computer, ensuring compliance with your organization's data security policies.

## Key Features

- Personalized email campaigns using spreadsheet data
- Individual attachments per recipient
- Dynamic CC and BCC recipients from spreadsheet
- Scheduled sending (specific day, time windows, delays between messages)
- Many-to-one mode (combine multiple rows into one email)
- Custom email headers and List-Unsubscribe support
- Fallback/default values for empty fields
- Works on Windows, Mac, and Web versions of Outlook

## Requirements

- Microsoft 365 Business subscription (free Outlook.com/Hotmail accounts not supported)
- A spreadsheet (Excel, CSV, etc.) with recipient data
- IT admin approval may be required for some organizations

## Getting Started

### Step 1: Prepare Your Spreadsheet

Create a spreadsheet with at least one column called "To" containing email addresses. Additional columns can contain any data you want to personalize (e.g., Name, Company, etc.). The first row must contain column headers.

Example spreadsheet structure:
```
To                  | Name    | Company
john@example.com    | John    | Acme Corp
jane@example.com    | Jane    | Beta Inc
```

### Step 2: Start the Add-In

1. Click "New Email" in Outlook
2. Find SecureMailMerge in the Apps menu (or add-ins ribbon)
3. Click to launch the add-in sidebar

### Step 3: Upload Your Spreadsheet

Click "Upload Spreadsheet" and select your file. The add-in will display the number of recipients found. Verify this matches your expectations.

### Step 4: Create Your Email Template

Write your email in the Outlook composer. To insert personalized content:
- Use the dropdown in the add-in to select a column
- Or type personalization tokens directly: `{{ColumnName}}`
- For column names with spaces: `{{ ["Column Name"] }}`

Personalization tokens work in both the subject line and email body.

### Step 5: Send Test Email

Click "Send Test" to receive a preview email using data from the first spreadsheet row. The email goes to you, not the recipient. Verify all tokens are replaced correctly.

### Step 6: Send Campaign

Click "Start Sending" to begin the campaign. Progress displays for each recipient. Emails appear in your Sent Items. You can pause and resume at any time.

## Advanced Use Cases

### Individual Attachments Per Recipient

Send different files to each recipient:

1. Add an "Attachments" column to your spreadsheet
2. Enter filenames (e.g., `contract.pdf`) for each recipient
3. Multiple files per recipient: separate with semicolons (`file1.pdf;file2.pdf`)
4. Upload all referenced files when prompted
5. Send your campaign

File names must match exactly (case-sensitive) between spreadsheet and uploaded files.

### CC and BCC Recipients

**Same CC/BCC for all emails:** Add recipients directly in the Outlook CC/BCC fields.

**Individual CC/BCC per recipient:** Add "CC" or "BCC" columns to your spreadsheet with email addresses. Multiple addresses: separate with semicolons.

**Combined approach:** Use both methods together - static recipients in Outlook fields plus dynamic ones from spreadsheet columns.

### Scheduled Sending

Access these options via "Show advanced campaign features" in the add-in:

**Send on a specific day:** Set a future date. Emails generate to your Drafts folder and send automatically on that date.

**Send during specific hours:** Set start and end times (e.g., 9:00-17:00 for business hours only).

**Delay between messages:** Add seconds between each email (1-600 seconds). Helps avoid spam filters. Note: Microsoft processes scheduled messages in ~30-second batches.

Your Outlook doesn't need to stay open once generation completes.

### Default/Fallback Values

Handle empty spreadsheet cells with default values:

```
{{ ColumnName | default: 'Default value' }}
{{ ["Column Name"] | default: 'Valued Customer' }}
```

### Individual Links Per Recipient

1. Add a column with unique URLs (e.g., "Link")
2. In Outlook, type link text and select it
3. Insert > Insert Link
4. Set the address to `{{Link}}`
5. If Outlook adds `https://`, remove it from your spreadsheet URLs

### Many-to-One Mode (Combine Multiple Rows)

Send one email containing data from multiple spreadsheet rows:

1. Use identical "To" values for rows you want combined
2. Upload spreadsheet - add-in detects duplicates
3. Select "Many-to-one" mode when prompted
4. Insert a table using the provided button
5. Regular tokens show comma-separated values from all rows
6. Attachments, CC, and BCC are automatically combined and deduplicated

### Custom Email Headers

Add custom headers for mail flow rules or List-Unsubscribe:

1. Open advanced campaign features
2. Custom headers must start with `x-` (e.g., `x-sent-by`)
3. For List-Unsubscribe: `<mailto:you@company.com?subject=unsubscribe>`
4. Headers support personalization tokens: `{{HeaderColumn}}`

### Read Receipts and Delivery Receipts

Enable read receipts, delivery receipts, or high importance flags in the advanced options. These use standard Outlook functionality.

## Personalization Token Syntax

Basic: `{{ColumnName}}`
With spaces: `{{ ["Column Name"] }}`
With default: `{{ ColumnName | default: 'fallback' }}`

Tokens work in:
- Email subject
- Email body
- CC/BCC fields (via spreadsheet columns)
- Hyperlink URLs
- Custom header values

## Troubleshooting

**Spreadsheet not loading:** Ensure first row has column headers, no empty rows/columns in the middle, and at least a "To" column exists.

**Tokens not replacing:** Check spelling matches column headers exactly. Send a test email to verify.

**Can't send:** Verify you're logged in with an account that has send permissions. Use the sign-out link if needed.

**Campaign interrupted:** Reopen the draft email and restart the add-in. It resumes from where it stopped.

## Links

- Website: https://www.securemailmerge.com
- Help Center: https://www.securemailmerge.com/help
- Install: https://www.securemailmerge.com/help/installing-securemailmerge-addin-for-outlook
- Pricing: https://www.securemailmerge.com/pricing
- IT Security Guide: https://www.securemailmerge.com/help/it-security