- Pfsense Office 365 Smtp Login
- Pfsense Office 365 Smtp Settings
- Pfsense Office 365 Smtp Address
- Pfsense Office 365 Smtp Server
Server Address: smtp.office365.com Username: Your Office 365 Address (e.g. [email protected]) Password: Your Office 365 Password Port Number: 587 (With TLS) Authentication: Required Sending Limits: 10,000 Emails a day To know more about Office 365 SMTP settings, Click here. This really does eliminate so much of the hassle with using an Office 365 SMTP account to send email. I really think that the app password is kind of hack, it's just another password that can be cracked! We are using Mailjet.
This is a quick post to remind me how to configure a pfSense appliance for e-mail notifications sent through Google GMAIL.
Configuration was quick and easy –
- E-mail server: smtp.gmail.com
- SMTP Port of E-mail server: 465
- Secure SMTP Connection: Enable SMTP over SSL/TLS ticked
- From E-mail address: [choose an appropriate e-mail]
- Notification E-mail address: [the e-mail you want to receive alerts on]
- Notification E-mail auth username: [GMAIL account you are authenticating with]
- Notification E-mail auth password: [password associated with the GMAIL notification account you are using]
- Notification E-mail auth mechanism: PLAIN
One thing of note – pfSense doesn’t have a nice menu system to let you pick and choose notifications, at least not at the time of writing. My hope is that over time this functionality expands so that I can enable specific notifications for events of interest. There are optional packages that can be installed that provide some notification options but I’m really hopeful that native functionality comes soon.
Total Access Emailer uses SMTP to send your emails from Microsoft Access. That requires you to have an SMTP email server that allows you to send emails from the FROM addresses you specify.
There are many SMTP server providers including your internal Exchange Server and public providers like Gmail, Office 365, and services from ISPs.
With Office 365, Microsoft hosts Outlook and your emails in the cloud eliminating the complexity of hosting and managing your own Exchange server. As part of the service, Office 365 includes an SMTP server that lets you send emails without using Outlook. This lets programs like Total Access Emailer send emails on your behalf.
Microsoft offers these pages on configuring and troubleshooting SMTP on Office 365:
Email from Any Email Address Based on IP Address
The Office 365 Exchange Server can be configured to allow SMTP Relay for specific IP addresses. This eliminates the need for a specific user name and password login.
For a fixed location like an office or web site, a specific IP address or set of IP addresses can be allowed to use the SMTP server. Once configured, you can send emails on behalf of all the email addresses in your account without setting delegation rules.
This lets you use the SMTP protocol with SMTP server name MyAccount.mail.protection.outlook.com.
For more information on configuring your Office 365 Connectors to your IP addresses, visit our support page:
Setup Office 365 for SMTP RelayAssuming your Office 365 account is configured, you can connect to the smtp.office365.com server with your email address and password, then email messages using your FROM address.
If you want to send emails using other email address as the FROM address (e.g. [email protected], [email protected], etc.), those email accounts must allow the Logon Name to send messages on its behalf. This is called Mailbox Delegation.
Go to the Exchange Administrator site
Pfsense Office 365 Smtp Login
From Office 365, with an administrator login, go to the Exchange Admin Center by choosing Admin from the drop down menu in the top left corner:
Scroll down the left border and under Admin Centers, choose Exchange:
From the Exchange Admin Center, choose Recipients from the left border:
A list of mailboxes appears on the right pane. Individual email accounts appear under Mailboxes. Groups and distribution lists appear under Groups:
Specify which Accounts can Send Emails for it
Select a mailbox that you want to allow another login to email on its behalf, and click the pencil (or double click it) to edit it. Then click on the Mailbox Delegation item on the left border:
In the Send As box, the [NT AUTHORITYSELF] indicates it can send emails on behalf of itself (this doesn't exist for Groups). To allow another account to send emails FROM this address, click on the [+] and add the email account(s). If you want to remove one, click on the [-].
Then press [Save].
This information is correct when this information was documented. Microsoft Exchange/Office 365 can change this at any time. If the information is out-of-date, please let us know.
Relay Authorization by IP Address
If your Office 365 Exchange server is authorized for your IP address, use this protocol:
- Connection Type: SMTP
- Server Name: MyAccount.mail.protection.outlook.com
- Port: 25
- No login name or password
To do this, create a text file in the folder where Total Access Emailer is installed called Temail.txt containing the name of any email address that's authorized to send emails through the account. See the Troubleshooting section below for more information on this.
Authorization by User Name and Password
This is the most common approach where you login with an email address and password that is authorized to send emails for multiple email addresses using Mailbox Delegation. The basics are:
- Connection Type: TLS
- Server Name: smtp.office365.com
- Port: 587 or 25
- The account login name (email address) and password
Setting SMTP Settings in Total Access Emailer
After entering the SMTP Settings and pressing [OK], Total Access Emailer validates the settings to see if it works. If it fails, a warning message appears describing the problem.
Pfsense Office 365 Smtp Settings
Troubleshooting
Here's the description of this error from the Microsoft page:
This error indicates that the device is trying to send an email from an address that doesn’t match the logon credentials. An example would be if your entered login credentials for [email protected] in your application settings but the application tries to send emails from [email protected]. If your application or printer behaves this way, use Office 365 SMTP relay because SMTP client submission does not support this scenario.
This could be due to a few reasons:
Your SMTP Server does not allow relay
Make sure your login credentials allows relay.
Pfsense Office 365 Smtp Address
Your SMTP Server does not allow testing with our default email FROM address
Pfsense Office 365 Smtp Server
The SMTP server is not allowing Total Access Emailer to test with its default FROM email address of [email protected]. This can be changed by specifying another email address to use in a Temail.txt file in the folder where Total Access Emailer is installed.
To ensure that your mail server is configured properly and Relay is enabled, Total Access Emailer sends a test message to a known email address at FMS ([email protected]). Your network or mail server security may not like this.
Fortunately, Total Access Emailer allows you to customize this email address:
- Create an ASCII text file called Temail.txt containing the name of the email address you would like to use.
- Put the file in the folder where Total Access Emailer is installed (or the location of the Total Access Emailer runtime library). The location of the file depends on how you are running Total Access Emailer.
- If you are using the add-in, place the file where Total Access Emailer is installed.
- If you are using the Professional Version and using VBA with the runtime library, place the file in the folder where the library is located. For more information, visit Adding the Total Access Emailer Runtime Library Reference to Your Database.
Total Access Emailer will now use your email address for the Relay test. This must be a valid email address and Relay must be enabled on your mail server for this test to succeed.
We are simplifying this process in a future version of Total Access Emailer.
This is caused by:
- The logon name (email address) and password are not valid. Make sure your values let you get into that email account. Maybe the password changed recently. Also make sure the SMTP mail server name is correct.
- The logon name is not authorized to relay messages. Your logon credentials may be correct, but the email account is not authorized to relay messages through the SMTP server. For instance, for Gmail, you need to set your email account to Allow less secure apps (Setting Google Gmail as the SMTP Server for Total Access Emailer).