Now that October 1 has arrived, Microsoft has started the process to permanently remove basic authentication from 7 email connection protocols. So what happens next? Well, for many organizations, not much. They’re the ones that have already transitioned to modern authentication. For others, some unpleasant surprises might lie ahead as people discover that stuff just doesn’t work anymore.
Microsoft revealed some interesting Exchange Online statistics at the MEC 2022 event. 300 K physical mailbox servers is a staggering amount, but 7.3 billion mailboxes might be even more surprising. Also at MEC we discovered more about the campaign to remove basic authentication from Exchange Online and how well Microsoft’s Greg Taylor can communicate in Irish when he presents about the deprecation of basic authentication.
The upcoming removal of support for basic authentication in seven Exchange Online connectivity protocols could mean trouble for some Office 365 tenants if they don’t take care to ensure that modern authentication is used for PowerShell connections. The old-style Remote PowerShell connection must be replaced with the Connect-ExchangeOnline cmdlet from the Exchange Online management module (aka the V2 module). Apart from anything else, this should improve the performance and robustness of scripts, especially after Microsoft finishes the work to remove the WinRM dependency for older cmdlets.
October 1, 2022, is when Microsoft begins the final process of removing support for basic authentication for 7 email connection protocols from Exchange Online. The process will take several months to complete, and when it’s done, Office 365 will be a safer place that attackers will find more difficult to penetrate. But it’s time for tenants to prepare, if you haven’t already done so, and we highlight some critical points from Microsoft’s most recent post on this topic.
Microsoft is removing TLS 1.0 and 1.1 from Microsoft 365. This has been well flagged, but tenants might not understand the impact on PowerShell scripts which send email using the Send-MailMessage cmdlet and SMTP AUTH. In a nutshell, unless you force PowerShell to use TLS 1.2, attempts to send messages via Exchange Online will fail. It’s time to check those scripts and ,consider how to move away from SMTP AUTH and Send-MailMessage.
The road to modern authentication for Exchange Online is littered with things to do. One action item is to check Apple iOS and iPad devices using Exchange ActiveSync to connect to mailboxes. If these devices were configured to connect to Exchange Online before iOS 12, they’re likely using basic authentication. Right now, the only way to move them to modern authentication is to remove Exchange from the mail app and add Exchange again. It’s a bump on the way to modern authentication in October 2022.
Last week’s announcement that Exchange Online will block basic authentication for multiple protocols on October 1, 2022, got some attention. Now the hard choices of what to do with clients and applications need to be made. To smoothen the path to remove basic authentication, Microsoft is making an exception for SMTP AUTH. Your scripts and multi-function devices will keep working after October 2022, but the writing is on the wall and eventually even SMTP AUTH will stop working.
October 1, 2022 will be a big day for Exchange Online tenants because that’s when Microsoft starts to disable basic authentication for connectivity protocols whether or not tenants want this to happen. This is a huge and fundamental change that’s being driven by the need to increase the overall security of Exchange Online and individual tenants, while also blocking common attacks seeking to compromise user accounts. With only a year to go, it’s time to start work on preparing everything that needs to be in place for the great October 1 switchoff.
The need to remove basic authentication from Exchange Online is underlined by a June 14 report from the Microsoft Threat Intelligence Center pointing to how attackers compromise mailboxes using antiquated protocols like POP3 and IMAP4 to connect to accounts which don’t use MFA. After accounts are penetrated, the attackers plant inbox rules to forward copies of interesting messages and use the information received to plan and execute business email compromise attacks. Tenant administrators still have some work to do to secure Exchange Online and Azure AD…
Microsoft wants to remove basic authentication from Exchange Online connection protocols. But pressures have forced Microsoft into a new strategy and away from the mid-2021 date for deprecation of basic authentication for five protocols. Instead, Microsoft will disable basic authentication for protocols where it’s not used, include four addition protocols in its target set, and pause action for tenants where basic authentication is in active use. When they restart, Microsoft will give tenants 12 months’ notice that basic authentication will be blocked for a protocol. You can argue that Microsoft should have pressed ahead with their original plan, but would widespread disruption of service be worth the benefit gained from blocking vulnerable protocols? Balancing risk versus reward is often not easy.
The Microsoft 365 admin center includes the ability to manage settings for the default Exchange Online authentication policy. You might have other policies to allow selective access with basic authentication to some protocols; these policies must be managed with PowerShell. Authentication policies are part of the journey to eliminate basic authentication from Exchange Online, now expected to happen in mid-2021.
The combination of Exchange Online and PowerShell allows Office 365 admins to send messages for all manner of reasons. These scripts depend on SMTP AUTH connections and change is coming in this area with the deprecation of basic authentication. It’s a good idea to take an inventory of scripts that send email, including those that use the .NET classes to do the job.
Covid-19 dealt a blow to Microsoft’s plans to remove basic authentication from 5 connection protocols for Exchange Online and forced them to postpone the removal from October 13, 2020 to sometime in the second quarter of 2021. The news is disappointing because basic authentication is a weakness exploited by many hackers. But you can’t plan for a pandemic and Office 365 tenants need more time to be ready for the deprecation.
Azure Active DIrectory is getting a slimmed-down background image to help with bandwidth-constrained locations. Office 365 tenants with custom backgrounds won’t see the change. Customizing the appearance of the sign-in screen is easy if you prepare. And to finish up, we have pointers to a set of videos about how Azure Active Directory authentication works.
Some doubt that Exchange Online will disable basic authentication for five email connection protocols in October 2020. The refrain is that it will be too hard for customers. Well, it might be hard to prepare to eliminate basic authentication, but if you don’t, your Office 365 tenant will be increasingly threatened by attacks that exploit known weaknesses.
Microsoft plans to disable basic authentication for five Exchange Online connection protocols on October 13, 2020. They’ve been clear on this point for several months and are now moving to deliver tools and provide guidance about what people should do about clients that use basic auth connections with Exchange Web Services, Exchange ActiveSync, IMAP4, POP3, and Remote PowerShell. Work is needed to make sure that clients are prepared for the switchover to modern authentication.
Microsoft has announced that basic authentication for multiple email connection protocols won’t be supported after October 13, 2020. You won’t be able to connect with EWS, EAS, IMAP4, POP3, or Remote PowerShell unless you use modern authentication. There’s just over a year to prepare, but there’s some work to be done.
Exchange Online protocol authentication policies control what protocols a user can connect to mailboxes with, but it would be much better if we didn’t have to worry about some old and insecure protocols. Azure Active Directory gives Office 365 tenants the chance to clamp down on IMAP4 and POP3 connections and close off some of the holes that attackers try to exploit. Microsoft says that this can lead to a 67% reduction in account compromises, so that’s a good thing.
Microsoft has released a preview of the cmdlet set to allow tenants to create and manage protocol authentication policies for Exchange Online. It’s a great chance to disable basic authentication and reduce the attack surface for password spraying.
{"id":null,"mode":"button","open_style":"in_modal","currency_code":"EUR","currency_symbol":"\u20ac","currency_type":"decimal","blank_flag_url":"https:\/\/office365itpros.com\/wp-content\/plugins\/tip-jar-wp\/\/assets\/images\/flags\/blank.gif","flag_sprite_url":"https:\/\/office365itpros.com\/wp-content\/plugins\/tip-jar-wp\/\/assets\/images\/flags\/flags.png","default_amount":100,"top_media_type":"featured_image","featured_image_url":"https:\/\/office365itpros.com\/wp-content\/uploads\/2022\/11\/cover-141x200.jpg","featured_embed":"","header_media":null,"file_download_attachment_data":null,"recurring_options_enabled":true,"recurring_options":{"never":{"selected":true,"after_output":"One time only"},"weekly":{"selected":false,"after_output":"Every week"},"monthly":{"selected":false,"after_output":"Every month"},"yearly":{"selected":false,"after_output":"Every year"}},"strings":{"current_user_email":"","current_user_name":"","link_text":"Virtual Tip Jar","complete_payment_button_error_text":"Check info and try again","payment_verb":"Pay","payment_request_label":"Office 365 for IT Pros","form_has_an_error":"Please check and fix the errors above","general_server_error":"Something isn't working right at the moment. Please try again.","form_title":"Office 365 for IT Pros","form_subtitle":null,"currency_search_text":"Country or Currency here","other_payment_option":"Other payment option","manage_payments_button_text":"Manage your payments","thank_you_message":"Thank you for supporting the work of Office 365 for IT Pros!","payment_confirmation_title":"Office 365 for IT Pros","receipt_title":"Your Receipt","print_receipt":"Print Receipt","email_receipt":"Email Receipt","email_receipt_sending":"Sending receipt...","email_receipt_success":"Email receipt successfully sent","email_receipt_failed":"Email receipt failed to send. Please try again.","receipt_payee":"Paid to","receipt_statement_descriptor":"This will show up on your statement as","receipt_date":"Date","receipt_transaction_id":"Transaction ID","receipt_transaction_amount":"Amount","refund_payer":"Refund from","login":"Log in to manage your payments","manage_payments":"Manage Payments","transactions_title":"Your Transactions","transaction_title":"Transaction Receipt","transaction_period":"Plan Period","arrangements_title":"Your Plans","arrangement_title":"Manage Plan","arrangement_details":"Plan Details","arrangement_id_title":"Plan ID","arrangement_payment_method_title":"Payment Method","arrangement_amount_title":"Plan Amount","arrangement_renewal_title":"Next renewal date","arrangement_action_cancel":"Cancel Plan","arrangement_action_cant_cancel":"Cancelling is currently not available.","arrangement_action_cancel_double":"Are you sure you'd like to cancel?","arrangement_cancelling":"Cancelling Plan...","arrangement_cancelled":"Plan Cancelled","arrangement_failed_to_cancel":"Failed to cancel plan","back_to_plans":"\u2190 Back to Plans","update_payment_method_verb":"Update","sca_auth_description":"Your have a pending renewal payment which requires authorization.","sca_auth_verb":"Authorize renewal payment","sca_authing_verb":"Authorizing payment","sca_authed_verb":"Payment successfully authorized!","sca_auth_failed":"Unable to authorize! Please try again.","login_button_text":"Log in","login_form_has_an_error":"Please check and fix the errors above","uppercase_search":"Search","lowercase_search":"search","uppercase_page":"Page","lowercase_page":"page","uppercase_items":"Items","lowercase_items":"items","uppercase_per":"Per","lowercase_per":"per","uppercase_of":"Of","lowercase_of":"of","back":"Back to plans","zip_code_placeholder":"Zip\/Postal Code","download_file_button_text":"Download File","input_field_instructions":{"tip_amount":{"placeholder_text":"How much would you like to tip?","initial":{"instruction_type":"normal","instruction_message":"How much would you like to tip? Choose any currency."},"empty":{"instruction_type":"error","instruction_message":"How much would you like to tip? Choose any currency."},"invalid_curency":{"instruction_type":"error","instruction_message":"Please choose a valid currency."}},"recurring":{"placeholder_text":"Recurring","initial":{"instruction_type":"normal","instruction_message":"How often would you like to give this?"},"success":{"instruction_type":"success","instruction_message":"How often would you like to give this?"},"empty":{"instruction_type":"error","instruction_message":"How often would you like to give this?"}},"name":{"placeholder_text":"Name on Credit Card","initial":{"instruction_type":"normal","instruction_message":"Enter the name on your card."},"success":{"instruction_type":"success","instruction_message":"Enter the name on your card."},"empty":{"instruction_type":"error","instruction_message":"Please enter the name on your card."}},"privacy_policy":{"terms_title":"Terms and conditions","terms_body":null,"terms_show_text":"View Terms","terms_hide_text":"Hide Terms","initial":{"instruction_type":"normal","instruction_message":"I agree to the terms."},"unchecked":{"instruction_type":"error","instruction_message":"Please agree to the terms."},"checked":{"instruction_type":"success","instruction_message":"I agree to the terms."}},"email":{"placeholder_text":"Your email address","initial":{"instruction_type":"normal","instruction_message":"Enter your email address"},"success":{"instruction_type":"success","instruction_message":"Enter your email address"},"blank":{"instruction_type":"error","instruction_message":"Enter your email address"},"not_an_email_address":{"instruction_type":"error","instruction_message":"Make sure you have entered a valid email address"}},"note_with_tip":{"placeholder_text":"Your note here...","initial":{"instruction_type":"normal","instruction_message":"Attach a note to your tip (optional)"},"empty":{"instruction_type":"normal","instruction_message":"Attach a note to your tip (optional)"},"not_empty_initial":{"instruction_type":"normal","instruction_message":"Attach a note to your tip (optional)"},"saving":{"instruction_type":"normal","instruction_message":"Saving note..."},"success":{"instruction_type":"success","instruction_message":"Note successfully saved!"},"error":{"instruction_type":"error","instruction_message":"Unable to save note note at this time. Please try again."}},"email_for_login_code":{"placeholder_text":"Your email address","initial":{"instruction_type":"normal","instruction_message":"Enter your email to log in."},"success":{"instruction_type":"success","instruction_message":"Enter your email to log in."},"blank":{"instruction_type":"error","instruction_message":"Enter your email to log in."},"empty":{"instruction_type":"error","instruction_message":"Enter your email to log in."}},"login_code":{"initial":{"instruction_type":"normal","instruction_message":"Check your email and enter the login code."},"success":{"instruction_type":"success","instruction_message":"Check your email and enter the login code."},"blank":{"instruction_type":"error","instruction_message":"Check your email and enter the login code."},"empty":{"instruction_type":"error","instruction_message":"Check your email and enter the login code."}},"stripe_all_in_one":{"initial":{"instruction_type":"normal","instruction_message":"Enter your credit card details here."},"empty":{"instruction_type":"error","instruction_message":"Enter your credit card details here."},"success":{"instruction_type":"normal","instruction_message":"Enter your credit card details here."},"invalid_number":{"instruction_type":"error","instruction_message":"The card number is not a valid credit card number."},"invalid_expiry_month":{"instruction_type":"error","instruction_message":"The card's expiration month is invalid."},"invalid_expiry_year":{"instruction_type":"error","instruction_message":"The card's expiration year is invalid."},"invalid_cvc":{"instruction_type":"error","instruction_message":"The card's security code is invalid."},"incorrect_number":{"instruction_type":"error","instruction_message":"The card number is incorrect."},"incomplete_number":{"instruction_type":"error","instruction_message":"The card number is incomplete."},"incomplete_cvc":{"instruction_type":"error","instruction_message":"The card's security code is incomplete."},"incomplete_expiry":{"instruction_type":"error","instruction_message":"The card's expiration date is incomplete."},"incomplete_zip":{"instruction_type":"error","instruction_message":"The card's zip code is incomplete."},"expired_card":{"instruction_type":"error","instruction_message":"The card has expired."},"incorrect_cvc":{"instruction_type":"error","instruction_message":"The card's security code is incorrect."},"incorrect_zip":{"instruction_type":"error","instruction_message":"The card's zip code failed validation."},"invalid_expiry_year_past":{"instruction_type":"error","instruction_message":"The card's expiration year is in the past"},"card_declined":{"instruction_type":"error","instruction_message":"The card was declined."},"missing":{"instruction_type":"error","instruction_message":"There is no card on a customer that is being charged."},"processing_error":{"instruction_type":"error","instruction_message":"An error occurred while processing the card."},"invalid_request_error":{"instruction_type":"error","instruction_message":"Unable to process this payment, please try again or use alternative method."},"invalid_sofort_country":{"instruction_type":"error","instruction_message":"The billing country is not accepted by SOFORT. Please try another country."}}}},"fetched_oembed_html":false}