SMTP Settings Definitions and Setup (latest 6.10 and higher)

Summary
This article explains how to configure SMTP settings in WeEstimate to ensure reliable delivery of approval notifications, customer documents, and internal emails.

Overview

WeEstimate uses SMTP (Simple Mail Transfer Protocol) to send system notifications, approval emails, and customer-facing documents. Correct configuration is required to prevent authentication errors, delivery failures, and rejected messages.

Email Types in WeEstimate

WeEstimate sends two different types of emails, each with distinct requirements.

Approval and Notification Emails

Purpose
Used for BIN passing notifications, approval requests, and status updates.

Key Characteristics
System-generated
Strict header validation
Requires authenticated SMTP

Recommended Configuration
Office 365 SMTP with authentication

Customer Document Emails (Send to Customer / Send to Self)

Purpose
Used to send quotes, contracts, and documents to customers or yourself.

Key Characteristics
Sent on behalf of individual users
May require flexible From headers

Recommended Configuration
Internal relay servers or authenticated SMTP, depending on environment

SMTP Settings Explained

SMTP Mail Enabled

• Description
  Master switch that enables or disables all email functionality in WeEstimate.
• Usage
  Must be enabled for any emails to send.

SMTP Address

• Description
  The hostname or IP address of your SMTP server.
• Examples
  smtp.office365.com
  smtp-relay.yourcompany.com
  smtp.gmail.com
• Notes
  Do not include http:// or port numbers.

SMTP Port

• Description
  Defines which port WeEstimate uses to connect to the SMTP server.
• Common Values
  587 for Office 365 and authenticated SMTP
  25 for internal relay servers
  465 for legacy SSL connections
• Recommendation
  Use port 587 for Office 365.

Use SSL

• Description
  Encrypts communication between WeEstimate and the SMTP server.
• Enable When
  Using Office 365
  Using port 587
  Required by IT security policy
• Disable When
  Using internal relay servers on port 25 (in most cases)

SMTP User

• Description
  Username used to authenticate with the SMTP server.
• Format
  Typically a full email address.
• Office 365 Notes
  Must be a licensed mailbox with SMTP access.

SMTP Password

• Description
  Password associated with the SMTP User account.
• Security Notes
  Keep credentials secure
  Rotate passwords regularly
  Office 365 with MFA may require an app-specific password

Enable SMTP Send As

• Description
  Controls whether emails are sent from a single system address or individual user addresses.
• When Enabled
  Emails are sent from the SMTP Connect As address
  Requires Send As permissions
  Recommended for approval and notification emails
  Reply-To is set to the user’s email
• When Disabled
  Emails are sent from each user’s email address
  Often required for customer document emails
  Less strict but may cause issues with Office 365

SMTP Connect As

• Description
  The From address used when Enable SMTP Send As is enabled.
• Examples
  notifications@yourcompany.com
  noreply@yourcompany.com
• Requirements
  SMTP User must have Send As or Send on Behalf permissions
  Address must be valid and authorized

Send SMTP to Self

• Description
  Allows test or document emails to be sent to your own email address.
• Purpose
  Useful for testing and validation without sending to customers.

Common Configuration Scenarios

Office 365 Authenticated SMTP

• Best For
  Approval and notification emails
• Recommended Settings
  SMTP Mail Enabled: Enabled
  SMTP Address: smtp.office365.com
  SMTP Port: 587
  Use SSL: Enabled
  SMTP User: notifications@yourcompany.com
  SMTP Password: Account password or app password
  Enable SMTP Send As: Enabled
  SMTP Connect As: notifications@yourcompany.com
• Requirements
  Valid mailbox
  Send As permissions
  App password if MFA is enabled

Internal SMTP Relay Server

• Best For
  Organizations with internal mail relay servers
• Recommended Settings
  SMTP Mail Enabled: Enabled
  SMTP Address: smtp-relay.yourcompany.com
  SMTP Port: 25
  Use SSL: Disabled (typical)
  SMTP User: Blank if authentication not required
  SMTP Password: Blank if authentication not required
  Enable SMTP Send As: Disabled
• Notes
  Most internal relay servers do not require authentication.

Mixed Environment (Approval and Document Emails)

• Issue
  Approval emails require strict Office 365 settings, while document emails may require flexible headers.
• Current Limitation
  WeEstimate supports only one SMTP configuration at a time.
• Temporary Workaround
  Configure SMTP for approval emails
  Send approval emails
  Update SMTP settings for document emails
  Recycle the approval server
  Send document emails
  Restore original SMTP settings
• Note
  Future enhancements are planned to support multiple SMTP configurations.

Testing SMTP Configuration

Steps

1. Save SMTP settings
2. Click Test
3. Enter a test email address
4. Confirm email delivery
5. Review any error messages

Common Error Messages

Mandatory From Header is missing or invalid (5.7.1)

• Cause
  Office 365 rejected the email due to mismatched From address.
• Resolution
  Enable SMTP Send As
  Verify Send As permissions
  Confirm SMTP Connect As address

Unable to connect to server

• Cause
  Incorrect server, port, or firewall restrictions.
• Resolution
  Verify SMTP address and port
  Check firewall rules
  Confirm SSL setting

Authentication failed

• Cause
  Incorrect username or password.
• Resolution
  Verify SMTP User format
  Confirm password
  Use app password if MFA is enabled
  Verify mailbox permissions

Best Practices

• Security
  Always use SSL for external servers
  Use dedicated notification mailboxes
  Limit account permissions
  Rotate credentials regularly
• Reliability
  Test after every change
  Monitor spam folders
  Document SMTP settings

Troubleshooting Checklist

1. Confirm SMTP Mail Enabled
2. Verify SMTP address and port
3. Confirm SSL setting
4. Verify credentials
5. Check Send As permissions
6. Review mail server logs
7. Confirm recipient addresses
8. Check firewall restrictions