Pro Mail SMTP vs The Events Calendar Outlook Import Fix

Pro Mail SMTP is a powerful WordPress plugin that enhances email deliverability by connecting your site to various email service providers. Configure multiple SMTP providers with automatic failover, track email performance with advanced analytics, receive proactive failure alerts, and ensure reliable email delivery with intelligent routing. ☁️ NEW in 1.7: Amazon SES Support – Connect to Amazon Simple Email Service for cost-effective, scalable email delivery. Configure with your AWS IAM credentials and choose from 20+ global regions. 📋 NEW in 1.7: Connection-Level Log Filtering – Email logs now record the exact connection used per email. The log filter dropdown lists your configured connections by name so you can quickly isolate delivery issues per provider setup. 🚨 Proactive Email Failure Alerts – Get instant notifications via Slack, Discord, Microsoft Teams, or custom webhooks when emails fail to deliver. Never miss a critical email delivery issue again! 📊 Advanced Analytics Dashboard – Monitor real-time provider performance, view detailed delivery metrics, and track email engagement with comprehensive analytics for Gmail, Mailgun, SendGrid, and more. 🎯 Enhanced Email Routing – Create sophisticated routing rules with advanced conditional logic, regex matching, and source application detection to ensure emails are delivered through the optimal provider. 🚀 Features Multiple Provider Support: Standard SMTP servers Gmail (with secure OAuth authentication) Microsoft Outlook (with OAuth authentication) Amazon SES (AWS IAM credentials, 20+ regions) Brevo (formerly Sendinblue) TurboSMTP SMTP2GO Mailgun SendGrid Postmark SparkPost And more… Smart Email Routing: Route emails through specific providers based on custom conditions Automatic failover system using priority levels Set conditions based on email type, recipient, or sending plugin Advanced conditional logic with multiple operators (contains, starts with, regex, etc.) Support for source application detection Proactive Alert System 🚨: Real-time email failure notifications Multi-channel alert support (Slack, Discord, Microsoft Teams, Custom Webhooks) Smart threshold-based alerts to prevent spam Consolidated failure reports when thresholds are reached Individual alerts for immediate critical failures Test alert functionality to verify configurations Comprehensive Logging: Track email status (sent, delivered, failed) View detailed error messages Filter logs by connection name, status, date range, and search Configurable log retention Email content inspection Email resend functionality from logs Full email header and body inspection Advanced Analytics Dashboard: Monitor provider performance metrics View delivery rates and engagement statistics Track email analytics per provider Regular summary reports Date range filtering and pagination Export capabilities for detailed analysis Enhanced Security & Authentication: OAuth 2.0 authentication for Gmail and Outlook Secure API key management SSL/TLS encryption support Connection validation and testing Advanced Settings: Custom From Email and From Name per routing condition Fallback to WordPress mail system Easy import from other SMTP plugins (WP Mail SMTP, Easy SMTP) Bulk email management and cleanup tools Multi-attachment support with various file types Configuration General Setup Navigate to Pro Mail SMTP → Settings Configure your default “From Email” and “From Name” Choose whether to enable email summaries and set your preferred frequency Adding Email Providers Go to Pro Mail SMTP → Providers Click Add Provider Select your email service provider Enter your credentials: For SMTP: Server, port, username, password, encryption type For API-based services: API key and required settings For OAuth services: Follow the authentication flow Set a priority level for each provider (lower numbers = higher priority) Test the connection before saving Email Routing (Optional) Navigate to Pro Mail SMTP → Email Router Create rules to route specific emails through particular providers Set conditions based on recipient email, source plugin, or other factors Use advanced operators like “contains”, “starts with”, “regex match”, etc. Configure custom sender email and name for specific routing conditions Proactive Email Alerts Setup Navigate to Pro Mail SMTP → Alerts Click Add New Alert to create your first alert configuration Choose your notification channel: Slack: Enter your Slack webhook URL Discord: Enter your Discord webhook URL Microsoft Teams: Enter your Teams webhook URL Custom Webhook: Enter any custom webhook endpoint Set your failure threshold: 0 = Immediate alerts for every failure 1+ = Consolidated alerts when threshold is reached Configure alert settings and test the connection Enable the alert and save your configuration Alert Features: * Smart Thresholds: Prevent notification spam with configurable failure thresholds * Consolidated Reports: When multiple failures occur, get summarized reports instead of individual alerts * Rich Formatting: Alerts include detailed failure information, provider details, and site context * Test Functionality: Verify your alert configuration with test notifications Third-Party Services Pro Mail SMTP connects to various third-party email service providers to send your WordPress site’s emails. When you configure and use these services, your site will transmit data to these external services. Below is information about each service: Google / Gmail Service Description: This integration allows your WordPress site to send emails using your Gmail or Google Workspace account via the official Google APIs, typically using OAuth 2.0 for secure authentication. What data is sent and when: Authentication: When you authorize the plugin to connect to your Google account, authentication data (such as OAuth 2.0 tokens, Client ID, and Client Secret, if applicable) is exchanged with Google’s authentication servers (e.g., https://accounts.google.com/o/oauth2/v2/auth, https://oauth2.googleapis.com/token) to securely link your account. This happens during the setup process for the Gmail mailer. Email Transmission: When an email is sent from your WordPress site using a configured Gmail connection, the email content (including sender address, recipient(s) address(es), subject, body, headers, and any attachments) is transmitted to Google’s email sending servers (e.g., https://www.googleapis.com/gmail/v1/users/me/messages/send) for delivery. Service Provider: Google LLC Terms of Service: You can find Google’s Terms of Service here: https://policies.google.com/terms Privacy Policy: Google’s Privacy Policy is available here: https://policies.google.com/privacy Brevo (formerly Sendinblue) Service Description: This integration allows your WordPress site to send emails using the Brevo (formerly Sendinblue) email service via their API. What data is sent and when: Authentication: When you configure the plugin to use Brevo, your API key is stored by the plugin. This API key is sent to Brevo’s API endpoints (e.g., https://api.brevo.com/v3/...) for authentication with each email sent from your WordPress site. Email Transmission: When an email is sent from your WordPress site using a configured Brevo connection, the email content (including sender address, recipient(s) address(es), subject, body, headers, and any attachments) is transmitted to Brevo’s servers for delivery. Service Provider: Brevo Terms of Service: You can find Brevo’s Terms of Use here: https://www.brevo.com/legal/termsofuse/ Privacy Policy: Brevo’s Privacy Policy is available here: https://www.brevo.com/legal/privacy-policy/ Microsoft / Outlook / Office 365 Service Description: This integration allows your WordPress site to send emails using your Outlook.com or Microsoft 365 account via Microsoft’s APIs, typically using OAuth 2.0 for secure authentication. What data is sent and when: Authentication: When you authorize the plugin to connect to your Microsoft account, authentication data (such as OAuth 2.0 tokens, Client ID, and Client Secret, if applicable) is exchanged with Microsoft’s authentication servers (e.g., https://login.microsoftonline.com/common/oauth2/v2.0/authorize, https://login.microsoftonline.com/common/oauth2/v2.0/token) to securely link your account. This happens during the setup process for the Outlook/Microsoft mailer. Email Transmission: When an email is sent from your WordPress site using a configured Microsoft connection, the email content (including sender address, recipient(s) address(es), subject, body, headers, and any attachments) is transmitted to Microsoft’s email sending servers (e.g., via the Microsoft Graph API) for delivery. Service Provider: Microsoft Corporation Terms of Service: You can find the Microsoft Services Agreement here: https://www.microsoft.com/en-us/servicesagreement/ Privacy Policy: Microsoft’s Privacy Statement is available here: https://privacy.microsoft.com/en-us/privacystatement Mailgun Service Description: This integration allows your WordPress site to send emails using the Mailgun email service via their API. What data is sent and when: Authentication: When you configure the plugin to use Mailgun, your API key and sending domain are stored by the plugin. The API key is sent to Mailgun’s API endpoints (e.g., https://api.mailgun.net/v3/...) for authentication with each email sent from your WordPress site. Email Transmission: When an email is sent from your WordPress site using a configured Mailgun connection, the email content (including sender address, recipient(s) address(es), subject, body, headers, and any attachments) is transmitted to Mailgun’s servers for delivery. Service Provider: Mailgun Technologies, Inc. Terms of Service: You can find Mailgun’s Terms of Service here: https://www.mailgun.com/terms/ Privacy Policy: Mailgun’s Privacy Policy is available here: https://www.mailgun.com/privacy-policy/ Postmark Service Description: This integration allows your WordPress site to send emails using the Postmark transactional email service via their API. What data is sent and when: Authentication: When you configure the plugin to use Postmark, your Server API Token is stored by the plugin. This token is sent to Postmark’s API endpoints (e.g., https://api.postmarkapp.com/email) for authentication with each email sent from your WordPress site. Email Transmission: When an email is sent from your WordPress site using a configured Postmark connection, the email content (including sender address, recipient(s) address(es), subject, body, headers, and any attachments) is transmitted to Postmark’s servers for delivery. Service Provider: Wildbit LLC (the company behind Postmark) Terms of Service: You can find Postmark’s Terms of Service here: https://postmarkapp.com/terms-of-service Privacy Policy: Wildbit’s Privacy Policy (covering Postmark) is available here: https://wildbit.com/privacy-policy SendGrid Service Description: This integration allows your WordPress site to send emails using the SendGrid email delivery service via their API. What data is sent and when: Authentication: When you configure the plugin to use SendGrid, your API key is stored by the plugin. This API key is sent to SendGrid’s API endpoints (e.g., https://api.sendgrid.com/v3/mail/send) for authentication with each email sent from your WordPress site. Email Transmission: When an email is sent from your WordPress site using a configured SendGrid connection, the email content (including sender address, recipient(s) address(es), subject, body, headers, and any attachments) is transmitted to SendGrid’s servers for delivery. Service Provider: Twilio Inc. (the company behind SendGrid) Terms of Service: You can find SendGrid’s Terms of Service here: https://sendgrid.com/policies/tos/ Privacy Policy: SendGrid’s Privacy Policy is available here: https://sendgrid.com/policies/privacy/ SMTP2GO Service Description: This integration allows your WordPress site to send emails using the SMTP2GO email delivery service via their API or SMTP. What data is sent and when (API Method): Authentication: When you configure the plugin to use SMTP2GO via API, your API key is stored by the plugin. This API key is sent to SMTP2GO’s API endpoints (e.g., https://api.smtp2go.com/v3/...) for authentication with each email sent. Email Transmission: When an email is sent using a configured SMTP2GO API connection, the email content (including sender address, recipient(s) address(es), subject, body, headers, and any attachments) is transmitted to SMTP2GO’s servers. What data is sent and when (SMTP Method): Authentication: If configured via SMTP, your SMTP credentials (hostname, port, username, password) are sent to SMTP2GO’s SMTP servers for authentication with each email. Email Transmission: When an email is sent using a configured SMTP2GO SMTP connection, the email content is transmitted to SMTP2GO’s SMTP servers. Service Provider: SMTP2GO Terms of Service: You can find SMTP2GO’s Terms of Service here: https://www.smtp2go.com/terms-of-service/ Privacy Policy: SMTP2GO’s Privacy Policy is available here: https://www.smtp2go.com/privacy-policy/ SparkPost Service Description: This integration allows your WordPress site to send emails using the SparkPost email delivery service via their API. What data is sent and when: Authentication: When you configure the plugin to use SparkPost, your API key is stored by the plugin. This API key is sent to SparkPost’s API endpoints (e.g., https://api.sparkpost.com/api/v1/...) for authentication with each email sent from your WordPress site. Email Transmission: When an email is sent from your WordPress site using a configured SparkPost connection, the email content (including sender address, recipient(s) address(es), subject, body, headers, and any attachments) is transmitted to SparkPost’s servers for delivery. Service Provider: Message Systems, Inc. (SparkPost) Terms of Service: You can find SparkPost’s Terms of Use here: https://www.sparkpost.com/policies/tou/ Privacy Policy: SparkPost’s Privacy Policy is available here: https://www.sparkpost.com/policies/privacy/ Amazon SES Service Description: This integration allows your WordPress site to send emails using Amazon Simple Email Service (SES) via the AWS API, authenticated with IAM Access Key credentials. What data is sent and when: Authentication: When you configure the plugin to use Amazon SES, your AWS IAM Access Key ID and Secret Access Key are stored by the plugin. These credentials are used to sign requests to Amazon SES API endpoints (e.g., https://email. .amazonaws.com) using AWS Signature Version 4. Email Transmission: When an email is sent from your WordPress site using a configured Amazon SES connection, the email content (including sender address, recipient(s) address(es), subject, body, headers, and any attachments) is transmitted to Amazon’s email sending servers for delivery. Service Provider: Amazon Web Services, Inc. Terms of Service: You can find the AWS Customer Agreement here: https://aws.amazon.com/agreement/ Privacy Policy: Amazon’s Privacy Notice is available here: https://aws.amazon.com/privacy/ TurboSMTP Service Description: This integration allows your WordPress site to send emails using the TurboSMTP transactional email service. What data is sent and when: Authentication: When you configure the plugin to use TurboSMTP, your API key (and potentially username/password) is stored by the plugin and sent to TurboSMTP’s API endpoint (e.g., https://api.turbo-smtp.com/api/v2/mail/send) for authentication with each email sent. Email Transmission: When an email is sent from your WordPress site using a configured TurboSMTP connection, the email content (including sender address, recipient(s) address(es), subject, body, headers, and any attachments) is transmitted to TurboSMTP’s servers for delivery. Service Provider: Delivery Media S.R.L. (the company behind TurboSMTP) Terms of Service: You can find TurboSMTP’s Terms and Conditions here: https://www.serversmtp.com/terms-and-conditions/ Privacy Policy: TurboSMTP’s Privacy Policy is available here: https://www.serversmtp.com/privacy-policy/ Other SMTP Servers (Generic SMTP) Service Description: This integration allows your WordPress site to send emails using any standard SMTP server you configure (e.g., your web host’s mail server, or other third-party SMTP providers not explicitly listed above). What data is sent and when: Authentication: When you configure a generic SMTP connection, your SMTP credentials (hostname, port, username, password, encryption type) are stored by the plugin. These credentials are sent to your configured SMTP server for authentication each time an email is sent from your WordPress site. We recommend using constants defined in wp-config.php for sensitive data like passwords where possible. Email Transmission: When an email is sent from your WordPress site using a configured generic SMTP connection, the email content (including sender address, recipient(s) address(es), subject, body, headers, and any attachments) is transmitted to your configured SMTP server for delivery. Service Provider: This will be the specific SMTP provider you have chosen to configure. Terms of Service & Privacy Policy: You are responsible for obtaining and reviewing the terms of service and …

The Events Calendar allows for the import of calendar events via download of a generated iCalendar file. This generated file contains the X-WR-CALNAME header, which is a valid header. Unfortunately Outlook chokes and will create a new calendar when it sees this header instead of adding the event(s) to the default Outlook calendar. This plugin removes that header from the generated iCalendar file.