Office 365 Basic Authentication Deprecation and Emailing from Hosted Applications

Basic Authentication and Emailing from Hosted Applications

Office 365 Settings to Check

With the announcement that SMTP Auth will continue to support Basic Authentication, there are a few settings in Office 365 that can still cause Basic Authentication to be disabled and cause issues with emailing from your hosted application. 

For Sage versions that do not support TLS 1.2 (see TLS 1.2 Compliance for Sage 100 and Sage 300 (gotomyerp.com)), you may also need to enable "Legacy Protocols" as outlined by this article Sage100 2018 or older unable to email using office365 (gotomyerp.com)
All of the below settings affect security in your Office 365 tenant and should be reviewed by your IT or an IT provider independently. gotomyerp is only providing this as a guide, from what we have found to work through our testing.

Security Defaults

All new Office 365 tenants automatically have Security Defaults enabled. When enabled, Security Defaults will disable Basic Authentication and enable Multi-Factor Authentication and some other recommended security settings. More information on what is enabled with Security Defaults can be found in the article Providing a default level of security in Azure Active Directory - Microsoft Entra | Microsoft Learn
To use Basic Authentication with SMTP Auth, Security Defaults must be disabled. The option to enable/disable Security Defaults can be found in the Azure AD Portal. You can log into the Azure AD portal by going to https://aad.portal.azure.com/. You will need to be logged in as an Administrator.
  1. Click on "Azure Active Directory"
  2. Click on "Properties" in the center menu pane
  3. Click on "Manage security defaults" in the Properties pane
  4. Set "Enable security defaults" to "No" in the right pane that opens

Basic Authentication settings in Modern Authentication

Another option you can check to make sure Basic Authentication is enabled for SMTP Auth is under the Modern Authentication settings in the Org settings page.
  1.  Expand "Settings" (if you do not see Settings, click on "Show All")
  2. Click on "Org Settings"
  3. In the center pane, under "Services" scroll down to "Modern authentication"
  4. In the fly out pane on the right, scroll down to "Authenticated SMTP" and confirm it is checked.

SMTP Auth on Individual Accounts

SMTP Auth can also be disabled at a user level. This option disables SMTP Auth completely, not just Basic Authentication, so it is a good option to check if SMTP Auth is also not working with Modern Authentication.
  1. Expand "Users"
  2. Click on "Active users"
  3. Click on the user you want to check
  4. In the fly out pane on the right under "Mail" click on "Manage email apps"
  5. Confirm that "Authenticated SMTP" is checked

Gmail or Google Workspaces

If you are using a gmail or google workspaces email account, you will need to check on the below before setting up your email.
  1. If 2FA is enabled on your email account, you must use an app password Sign in with app passwords - Google Account Help.
  2. If you do not have 2FA enabled, then you will need to enable Less secure apps & your Google Account - Google Account Help
On personal Gmail accounts, you may be unable to enable less secure apps. If this is the case, we would recommend setting up 2FA or looking into upgrading your application to a newer version

For Newer Applications that support OAuth or other Modern Authentication

For Sage 100 2021.4 and QuickBooks 2021 and newer, please follow the email setup instructions in our How to email from Quickbooks and other applications (gotomyerp.com) article.

For Older Applications that do not support OAuth or other Modern Authentication

Below are options for Sage 100 and QuickBooks versions older than 2021. 
Upgrading to a supported version (i.e. Sage 100 2021.4, QuickBooks 2022) is recommended, as this will ensure you are using the latest security protocols and authentication methods. Please check with your consultant and contact sales@gotomyerp.com for additional information on an upgrade.

Option 2: SMTP with Basic Auth setup

QuickBooks older than 2021
In order to configure email in QuickBooks, do the following
  1. Login to QuickBooks --> Edit --> Preferences --> Send Forms --> ADD --> Change Email Provider to Others 
  2. Now enter the following and click OK
    • Your Email Id : This is your email address 
    • Server Name : This is the server name
    • Port: This is your Mail Server / SMTP Port Number 
    • SSL/TLS : Depending on your mail server you might have to check or uncheck the option
                       
You will be prompted for your email password when you send an email. You would enter your AppPassword here if you have MFA/2FA enabled on your account. It will save the password for that session, but once you close out of QuickBooks, you will need to reenter your password the first time you send an email.

Sage 100 2021.3 or older

  1. Login to Sage --> Open Library Master --> Main menu --> Company Maintenance --> Access the E-mail tab
  2. Now enter the following
    • Address : Mail server/SMTP Address
    • Port : Port number of your mail server
    • SMTP Encryption : Depending on your mail server you need to select one of them
    • User ID : This is generally your email address
    • Domain : This could be your email domain name, or your window domain name, some mail servers do not need this field
    • Password & Confirm Password : Both are your email password
                        

Option 3: SMTP Service Setup

gotomyerp is in no way affiliated with any of the third party SMTP services mentioned below.  We are providing this information as a courtesy workaround to our clients.  The use of any of the mentioned SMTP services or any other SMTP service not mentioned is the sole responsibility of the customer. We would recommend consulting with your IT or an IT service provider to find out what works best for you and your organization.

You can use a third party SMTP service (i.e. SMTP2GO, SendGrid), as this does not require authentication to your Office 365 and is only used for sending emails.

What you need:
  1. Access to your domain Name Server hosting your DNS. (Usually the same as your domain registrar, but not always)
  2. Add CNAME/TXT SPF records to authenticate your domain
Refer to the SMTP Server Setup section below for specific instructions on each of the aforementioned services.

SMTP Service Setup

SMTP services are only meant for sending emails and are in no way tied to your Office 365 email. You will not see the sent email in your Office 365 or your sent items.  The only way to track emails sent via this method is from the providers dashboard. You are not attaching these services to a specific mailbox, which allows you to send as any email address as long as it includes your domain.
The email does not need to exist in your Office 365 or any other email provider, it can be any email address as long as it ends in the verified domain name (i.e. this_email_is_not_real@myverifieddomain.com). Be mindful of who you are allowing to use the service, as it can be abused.
Below are the basic instructions to get started and emailing from Sage 100, QuickBooks or other applications. We recommend that you or your IT explore additional settings to comply with your security policies.
The only option that will work for QuickBooks is SMTP2GO with SMTP Users option, as QuickBooks requires a username in the format of an email address and a password

SMTP2GO

  1. Once signed into your account got to (1)Settings > (2)Verified Senders and click on (3)Add Sender Domain and enter your domain and click (4)Continue with this domain.
  2. Log into your DNS hosting provider and enter the CNAME values provided. Make sure "Enable hosted SSL" is selected. Once the DNS entries have been entered, allow at least 5 minutes to pass and then click on Verify
  3. If verification is complete you will see a green checkmark beside each CNAME entry in SMTP2GO. If it does not verify successfully, try again in 10 minutes or confirm that the DNS entries were entered properly. Due to the large amount DNS providers we are unable to provide instructions on how they should be entered, you will need to consult your providers documentation.
  4. Once the domain is verified, there are two options for setting up your emails. SMTP Users and IP Authentication. 
    1. SMTP Users provides more control, as you can assign user names and password to users.
    2. IP Authentication will allow any Sage user to send email from the hosted server, and does not require a user name or password.  
  5. Setting up SMTP Users: 
    1.  Under (1)Settings, click on (2)SMTP Users and then (3)Add SMTP User
    2. Enter in your desired (1)Username, (2)Password (these are auto generated, but can be changed) and (3)Description (optional) and then click on (4)Add SMTP User. 
      Note:
      For QuickBooks you will need to enter in a username in the format of an email.
    3. In the Sage email preferences enter in the following information:
      (1)Address: mail.smtp2go.com
      (2)Port: 587 (must use this port)
      (3)SMTP Encryption: TLS/STARTTLS
      (4)User ID: Username created in step b
      (5)Password: password created in step b
      Click on Accept to save your configuration. You can also click on "Test E-mail" before saving to confirm the relay is working properly. You can use any email as long as it is belongs to your domain, the email address is not required to have a mailbox, as this is just meant for sending.

      In the QuickBooks email setup Edit > Preferences > Send Forms, click add and enter in the following information.
      (1)Email ID: Username created in step b (must be in an email format) 
      (2)Email Provider:
      Others
      (3)Server Name:
      mail.smtp2go.com
      (4)Port:
      587 (Must be use this port)
      Check (5)SSL/TLS and then click on (6)OK
      When you send your first email, you will be promted for the password that you created in the step b


  6. Setting up IP Authentication
    Before starting, you will need the public IP address of your server, please contact support@gotomyerp.com to obtain the IP Address. Please state that it is to be used for SMTP2GO IP Authentication.
    NOTE: IP Authentication will not work in QuickBooks as it requires a email address as a username. 
    1. Under (1)Settings, click on (2)IP Authentication and then (3)Continue
    2. Click on Add IP Address
    3. Enter the (1)IP address that is provided by support and a (2)Description (optional). 
    4. In the Sage email preferences enter in the following information:
      (1)Address: mail.smtp2go.com
      (2)Port: 587 (must use this port)
      (3)SMTP Encryption: TLS/STARTTLS
      Click on Accept to save your configuration. You can also click on "Test E-mail" before saving to confirm the relay is working properly. You can use any email as long as it is belongs to your domain, the email address is not required to have a mailbox, as this is just meant for sending.

SendGrid

SendGrid will only work with Sage, as you are able to provide a username other than an email. SendGrid will not work with QuickBooks.

  1. Go to Email Delivery, API, Marketing Service | SendGrid and create your account.
  2. Once signed into your account go to (1)Settings > (2)Sender Authentication and then select (3)Get Started under "Authenticate Your Domain"
    NOTE: 
    Additional setup information can be found here How to set up domain authentication | Twilio (sendgrid.com)

  3. Select your DNS hosting provider. If your provider is not listed select "Other Host (Not Listed)". Select if you would like to brand your links for your domain, additional info can be found here How to set up link branding | Twilio (sendgrid.com). For the purpose of this guide we will select "No". Click "Next" once the options have been selected


  4. Enter your (1)domain name in the next screen and click on (2)Next
  5. Log into your DNS provider and enter the records provided. Wait about 5 mins and then select "I've added these records." and click on Verify.
  6. You should then get a screen that confirms that the domain was verified, click on "Return to Sender Authentication". You should also see a "Verified" status next to your domain name. If it does not verify successfully, try again in 10 minutes or confirm that the DNS entries were entered properly. Due to the large amount DNS providers we are unable to provide instructions on how they should be entered, you will need to consult your providers documentation.

  7. Once verified, click on (1)Email API > (2)Integration Guide and click on (3)Choose under SMTP Relay
  8. Enter a name for your (1)API key and click Create Key. You will them be presented with the API key and (2)Password will get populated with that key.
    NOTE: Copy the API key and store it in a safe location, you will not be able to retrieve it afterwards.
    Before selecting (3)"I've updated my settings" Next: Verify Integration, copy the API key and setup your hosted applciation. 
  9. Open the email preferences in Sage
    Enter in the following information:
    (1)Addresssmtp.sendgrid.net
    (2)Port: 587 (must use this port)
    (3)SMTP Encryption: TLS/STARTTLS
    (4)User ID: apikey
    (5)Password: <apikey provided in the above step>
    Select (3)"I've updated my settings" Next: Verify Integration in SendGrid


  10. In Sage email setting click on "Test E-mail" and enter in (1)From E-mail Address, (2)Subject Line for Test and (3)E-mail Addresses then click on (4)Send
  11. If you do not get an error in Sage 100 on the test email, click on "Verify Integration" in SendGrid. You should then shortly see a success message.

  12. Click "Accept" in Sage email setting to save your email.


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