WordPress Send Mail Via Smtp – In the article – Configure your WordPress site to send email through an anonymous session on Exchange Online (Office 365) | In Section 2#6, we review the necessary settings, in a scenario where we want to configure our WordPress site to target the Office 365 mail server using the SMTP protocol without authentication (aka, the user without providing credibility).
This setting will result in a scenario where e-mails sent to users of our organization will be classified as “spam mail”.
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In the article – Building Exchange Online Spam Spam Rules – Exclusive Sender Email Address Whitelist | In Part 3#6, we will learn how to avoid this “result” by creating a rule that “whitelists” the sender’s email address.
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In the article – Configure Your WordPress Site to Send Email to User Credentials via Exchange Online (Office 365) | Section 4#6, we review the required settings, in a scenario where we want to configure our WordPress site, using the TLS protocol + providing user authentication to reach the Office 365 mail servers.
In the article – Set up a WordPress site to send email through Exchange Online (Office 365) | Office 365 | Provide User Credentials Without Licensing Part 5#6, we reviewed a method we could use to save the cost of purchasing Office 365 licenses for our WordPress site users for authentication purposes.
In the article – Set up your WordPress site to send email through GoDaddy Mail Server – Shared Hosting Plans | In Section 6#6, we reviewed the settings required in a scenario where we want to configure our WordPress site using a shared hosting plan to target GoDaddy’s mail server.
The task of successfully managing our WordPress site configuration on an email server address presented us with a number of challenges.
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The main challenge is – our need, to be familiar with the specific requirements of the email infrastructure we need, and the network architecture, which hosts our WordPress site.
Obviously, the settings in WordPress seem very simple because we use a graphical interface, but the “catch” is that in many scenarios, we don’t really know what are the configuration parameters required by the destination mail infrastructure. .
In this diagram, we can see an example of the different “mail components” that we need to know about the mail server we want to address.
The default communication protocol that we usually use is the SMTP protocol. The SMTP protocol is an unencrypted protocol. In some scenarios, we will use the TLS mail protocol because the TLS protocol encrypts the communication channel between the two endpoints.
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In case we want to use (or need to use) the TLS mail protocol there are additional elements that we need to be concerned about such as
For example, in a scenario where we want to configure our WordPress site to target Exchange Online as a mail server using TLS, the supported version of TLS is TLS 1.0 and above.
From my own experience, many WordPress plugins do not support the required version of TLS or have other issues when trying to resolve exchanges online using TLS.
The TLS protocol can be configured using advanced settings, such as certificate usage conditions, the requirement that the certificate must include a unique hostname, and more. These conditions can be considered as optional or mandatory conditions.
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For example, in a scenario where we want to configure our WordPress site to target Exchange Online as a mail server using TLS, Exchange Online does not enforce a prerequisite where the mail server Communication requires the use of a certificate. .
In other words, in a scenario where we need to reach Exchange Online using TLS, we don’t need to use a “client-side” certificate.
We will need to verify that we know the port number used by the email server we need.
The most important issue to consider regarding the communication protocol port number is the existing firewall policy.
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For example, in many scenarios, the reason for “mail communication failure” is related to the fact that the existing firewall infrastructure that “protects” our WordPress site, does not allow our web server to use the SMTP (port ) to communicate with external hosts using ). 25) or TLS (port 587) protocol.
We will need to verify that the existing network where we host our WordPress site, allows such outbound email communications.
In the article – Configure your WordPress site to send email through Exchange Online (Office 365) using TLS | In Part 4#6, we will review how to verify communication from a destination mail server using a special feature of the Postman SMTP Mailer/Email Log plugin.
The communication channel between the email client (a WordPress site in our scenario) and the mail server can be implemented as an “unauthenticated” session or an “authenticated session”.
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An e-mail server can “enforce” a binding mode, where it is willing to accept requests from e-mail clients only if the e-mail client proves its identity by providing user credentials. Another scenario could be – a scenario where the mail server wants to accept anonymous mail delivery requests.
Example 1 – In a scenario where we want to configure Exchange Online as a mail server, we can target the Exchange Online mail server without providing user credentials or with user credentials (we will explain later Let’s see why it is the best option – providing user credentials). ).
Example 2 – In a scenario where a WordPress site is hosted on GoDaddy using a shared hosting plan, we don’t need to provide user credentials.
Other Subject Matter Elements – An authentication session is an authentication protocol required by a mail server.
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For example, when we address Exchange Online as a mail server, and we want to provide user credentials, then Exchange Online will “agree” to accept user credentials only if we use the TLS protocol. Set up a session using
Although these “conditions” seem like an obvious requirement, in reality, you will find that they are not so “obvious”.
In case we want to point to the Office 365 Mail infrastructure, we can point to the “Office 365 Mail Server” using one of the following “entities”:
In case we configure the WordPress Mail plugin to connect to Exchange Online using SMTP, the hostname we need to use is – the hostname of the “Office 365 MX file” “appears as
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If you need more information, you can read the article – What is the file name of my Office 365 MX?
I will demonstrate this setup in the article – Configuring your WordPress site to send email through an anonymous session on Exchange Online (Office 365) | Part 2#6
In case we configure the WordPress Mail plugin to connect to Exchange Online using authenticated sessions + using the TLS protocol, the hostname we need to use.
The characters in this scenario are WordPress sites hosted on some web hosting provider like GoDaddy.
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In this type of scenario, the general network infrastructure is implemented by the mail server that the web hosting provider “exposes” for their customers to use.
For customers using a GoDaddy shared hosting plan, the mail server provided by GoDaddy is called – relay-hosting.secureserver.net
I will demonstrate this setup in the article – Configure Your WordPress Site to Send Emails Through GoDaddy Mail Server – Shared Hosting Plans | Section 6
Generally, the preferred communication channel between the mail client (a WordPress site in our scenario), and the mail server should be implemented as an “authenticated session”.
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In other words, the email client must provide user credentials before initiating an SMTP session with the mail server.
If the email client provides its credentials, the email server can “submit” the email client, and trust the email client’s requests to deliver to email receiving organizations or external email recipients.
There are two main advantages to a scenario where we configure an email client to provide user authentication:
Option 1 – In the case of an email client (WordPress site), configured to provide user credentials, the email sent will be considered “legitimate email” because the organization (
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Option 2 – In case the email client (WordPress site) is not configured to provide user authentication (anonymous connection), the email sent will be considered “illegal email” because the sender (
) “claims” to be a legitimate sending organization, but cannot prove its identity. In this case, the result can be rejected by email
When we point to our e-mail server and ask it to “forward” e-mail to an external recipient, (a recipient whose e-mail has a domain name not hosted by our e-mail server) the mail From the server’s point of view, the way to submit. email
By default, most email servers are configured to “accept” email delivery requests, only if the email client is considered a “trusted email client”. In other words, only if the recipient of the email can prove their identity by providing legitimate user credentials.
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