Gmail to Microsoft 365 Migration Issue Open for 7+ Days – Seeking Guidance or Escalation Path
I’m facing an issue with a Gmail to Microsoft 365 migration that has been open for more than 7 days, and I’m looking for guidance or an escalation path from the community. Scenario: Migration type: Gmail to Microsoft 365 Issue started: April 22 Current status: Stuck with no clear resolution What’s happening: The support ticket has been active since April 22. However, the updates I’ve been receiving are generic responses such as “we are working on it” and “this has been prioritized.” Despite multiple follow-ups, there has been: No clear root cause identified No ETA provided No technical breakdown of the issue I also requested a callback from the assigned manager and technical lead to better understand the situation, but the communication has remained email-only with repeated status updates. What I’m looking for: Has anyone faced similar issues during Gmail → Microsoft 365 migrations? Are there known blockers or common causes that could lead to this kind of delay? What is the recommended escalation path when support is unable to provide technical clarity or ETA? Any insights, workarounds, or guidance would be highly appreciated. Thank you in advance.
Apple Mail EWS sync intermittent after EwsEnabled=True + AppID allow list
We're a small Microsoft 365 Business tenant (Exchange Online Plan 1/2 mix). One user's Apple Mail (macOS, Exchange/EWS account) intermittently stops syncing new mail — Connection Doctor shows a healthy green "Connection and login to server succeeded," but Get New Mail/manual fetch and forced Sync All Accounts return nothing new, while the same mail is already present via ActiveSync on the same user's iPhone/iPad. Symptoms recur every 1–3 days after temporarily resolving. Troubleshooting completed so far: - Confirmed autodiscover/External URL correctly resolves to outlook.office365.com/EWS/Exchange.asmx - Confirmed EWS enabled at the mailbox level (Manage email apps in admin center) - Found EwsEnabled was blank/null at the org level — set to $true via Set-OrganizationConfig - Configured EwsAllowedAppIDs to include Apple's app ID (f8d98a96-0999-43f5-8af3-69971c7bb423, "Apple Internet Accounts") - Fully removed and re-added the Mac Mail account after the above org-level change - Restarted the Mac, tried DNS changes (8.8.8.8/8.8.4.4), ruled out router-level filtering - Verified no antivirus/VPN/security software on this Mac's network Despite all this, the issue persists intermittently. Notably, a second mailbox on the same tenant, used with Apple Mail on a different Mac (different macOS version, different physical location/network), does NOT experience this issue — so it doesn't appear to be a blanket tenant-wide EWS disruption. Given Apple Mail's continued reliance on EWS ahead of the October 2026 phased disablement, and Microsoft's acknowledgment that Apple Mail for Mac is a heavy EWS consumer they're working with Apple to migrate to Graph, I'm wondering: 1. Could this be related to the ongoing "scream test" EWS disruption testing Microsoft has mentioned, and if so, is there a way to check whether a specific mailbox has been included in that testing? 2. Any known differences in EWS session/connection handling between macOS versions that could explain one Mac being affected and not the other? 3. Anything else worth checking tenant-side (throttling policies, CAS mailbox settings, conditional access rules) that could apply per-mailbox rather than tenant-wide? Happy to provide EWS usage report data or run any diagnostic commands if it helps others hitting the same thing before October.Reference Architecture for an On-Premises AI Assistant for Microsoft Exchange.
Bringing Secure AI Capabilities to On-Premises Microsoft Exchange Many organisations continue to operate Microsoft Exchange within their own data centres because of regulatory requirements, data-residency policies, security considerations, operational dependencies, or the need to maintain complete control over sensitive email information. At the same time, users increasingly expect Artificial Intelligence to help them manage growing email volumes, understand long conversation threads, locate information quickly, analyse attachments, and prepare relevant responses. This creates an important question: Can organisations introduce AI-assisted email capabilities without migrating their on-premises Exchange environment or sending email data to public AI services? With the right architecture, the answer is yes. The opportunity for AI in on-premises Exchange Users spend a significant amount of time reading lengthy email chains, searching for previous discussions, identifying action items, reviewing attachments, and preparing responses. An AI-powered email assistant can help reduce this effort while continuing to operate within the organisation’s controlled infrastructure. Such a solution can be integrated with Microsoft Exchange through an Outlook Web App, or OWA, Add-In. The Add-In provides AI-assisted capabilities within the familiar Outlook Web interface and can be centrally deployed to selected users or Active Directory groups by the Exchange administrator. The purpose is not to replace Exchange or change the way emails are managed. Instead, it introduces an intelligence layer that helps authorised users interact more efficiently with the email information they are already permitted to access. Key capabilities of an AI-powered Exchange Email Assistant 1. Email and conversation summarisation The assistant can summarise an individual email or an entire conversation thread. Instead of reading every message in a long chain, the user can receive a structured summary covering: The purpose of the conversation. Important decisions and commitments. Key action items. Deadlines and pending responses. Relevant information available in attachments. The summarisation process can consider both incoming and sent messages so that the complete context of the conversation is preserved. 2. Contextual draft reply generation The assistant can prepare a suggested response based on the complete email thread and the user’s instructions. Users may select an appropriate tone, such as: Formal. Neutral. Technical. The generated response is placed in the user’s Exchange Draft folder or displayed for review within the OWA Add-In. A critical control is that the AI assistant does not independently send the email. The user remains responsible for reviewing, editing, approving, and sending the response. This human-review approach helps organisations adopt AI while retaining accountability over external and internal communications. 3. Natural-language mailbox search Traditional mailbox search generally depends on exact keywords, sender names, subjects, or date filters. An AI-enabled search experience allows users to search their mailbox using natural-language questions, such as: “Find emails received last month regarding the infrastructure renewal.” “Show unread emails from the finance team that require my approval.” “Find the discussion where the customer confirmed the delivery date.” “Summarise emails from a particular sender concerning the purchase order.” The solution can combine semantic search with traditional keyword-based search to improve the relevance of results. Users can also apply filters such as sender, subject, date range, read or unread status, and conversation thread. 4. Attachment analysis and OCR Important information is often contained within email attachments rather than the email body itself. An on-premises AI assistant can process supported documents, including: PDF files. Microsoft Word documents. Microsoft Excel files. Scanned documents. Image-based attachments. Optical Character Recognition, or OCR, can be used to extract information from scanned or image-based documents. The extracted content can then support email summarisation, contextual draft generation, and mailbox search. For example, a user may ask the assistant to prepare a response based on the commercial terms or delivery date mentioned in an attached document. Maintaining strict mailbox privacy Mailbox privacy is one of the most important architectural considerations for an enterprise AI email assistant. Each user must only be able to access and process emails from their own authorised mailbox. Information retrieved from one user’s mailbox must never become available to another user. This isolation should be enforced across every layer of the solution, including: User authentication. Exchange access tokens. Application sessions. Search indexes. Vector embeddings. AI prompts and responses. Cache and temporary data. Audit logs. The backend should validate the authenticated user and verify mailbox ownership for every request made to Exchange. Where vector search is used, mailbox data should be stored in user-isolated collections, partitions, or namespaces. This helps prevent cross-user retrieval at the data layer rather than relying only on controls within the user interface. Operating without public cloud AI services For organisations with strict security or data-sovereignty requirements, the AI models and supporting components can be deployed within the customer’s infrastructure. A fully on-premises architecture may include: A locally hosted Large Language Model. An on-premises embedding model. A re-ranking model. A vector database. A keyword-search engine. A backend API layer. An OCR or document-intelligence service. A secured OWA Add-In. Integration with Active Directory. Audit, monitoring, and administrative controls. The entire solution can operate within an internal network without sending email content, attachments, prompts, or generated responses to public AI platforms. This model can also support air-gapped environments where internet access is either restricted or completely unavailable. Centralised deployment and administration The OWA Add-In can be deployed centrally through Exchange administration controls. Administrators can assign the Add-In only to selected users or security groups. Employees who are not assigned the solution will not see the AI assistant within their Outlook Web interface. Administrative controls may include: User and group assignment. Enabling or disabling individual AI features. Summarisation-only mode. Draft-generation controls. Attachment-size restrictions. Session and retention policies. Model and performance settings. Usage monitoring. Audit logs. Resource utilisation monitoring. These controls allow organisations to begin with a limited group of users and gradually extend the solution after validating performance, security, and user adoption. Security and governance considerations Introducing AI into an enterprise email environment requires more than deploying a language model. The complete solution should be designed around security, privacy, governance, and responsible AI principles. Important considerations include: Authentication and authorisation The solution should integrate with the organisation’s existing identity infrastructure, such as Active Directory, and enforce role-based access controls. Encryption Email content, attachments, indexes, logs, and other sensitive information should be encrypted both in transit and at rest. Data retention Organisations should clearly define whether AI prompts, generated summaries, and draft content are retained. In privacy-sensitive environments, generated content may remain available only for the active session and should not be permanently stored by the AI application. Auditability The system should record relevant operational events, such as the user identity, requested function, timestamp, and processing status. Depending on the organisation’s policy, the actual email or generated response content may be excluded from audit logs. Human oversight AI-generated responses should be treated as suggestions. The user must review and approve them before sending. The assistant should also disclose its limitations and avoid presenting uncertain outputs as confirmed facts. Performance and capacity On-premises AI processing depends on available compute, memory, storage, and GPU resources. The architecture should account for: Number of concurrent users. Average mailbox size. Volume and size of attachments. Expected response time. Model size. Search-index growth. OCR processing requirements. High availability and backup requirements. A practical adoption approach Organisations do not need to introduce all capabilities at once. A controlled proof of concept can begin with a limited number of users and a defined set of features. A practical implementation sequence may include: Phase 1: Email summarisation Start with individual email and conversation-thread summaries. This provides immediate value while keeping the initial architecture relatively focused. Phase 2: Contextual draft replies Introduce draft generation with mandatory user review and clearly defined tone controls. Phase 3: Attachment processing Enable OCR and document parsing for supported attachments. Phase 4: Intelligent mailbox search Index authorised mailbox content and introduce natural-language search with strict per-user isolation. Phase 5: Wider deployment After security testing, performance validation, and user feedback, extend the solution to additional departments or user groups. Conclusion Organisations operating on-premises Microsoft Exchange do not necessarily need to choose between maintaining control over their email environment and adopting AI-assisted productivity capabilities. A carefully designed on-premises AI email assistant can support email summarisation, contextual draft preparation, attachment analysis, and natural-language mailbox search while keeping sensitive information within the organisation’s infrastructure. The most important success factors are not limited to the AI model itself. Identity controls, mailbox isolation, human approval, auditing, infrastructure sizing, and data-governance policies are equally important. For organisations evaluating private, sovereign, or air-gapped AI, on-premises Exchange can become an effective starting point for introducing practical AI capabilities in a secure and controlled manner. Connect with us to implement this solution in your organization. About the Author Vinay Prakash is the CEO of Glorious Insight and an Ex Microsoft Employee. He works with organisations on Data, Artificial Intelligence, Microsoft cloud technologies, enterprise applications, and secure on-premises AI solutions. For technical discussions related to private or on-premises AI adoption, he can be reached at: Email: email address removed for privacy reasons
Proper whitelisting of microsoft.com on dnswl.org
I keep having the issue that system-generated e-mails, e.g. on Trace Reports get classified as spam by the receiving e-mail provider. The sender address is email address removed for privacy reasons and the e-mails go to my M365 mailbox and are redirected to my external monitoring mailbox with that e-mail provider. The e-mail provider calculates a score that includes checking the sender's IP address 52.101.69.91 with dnswl.org . Unfortunately, that address is only whitelisted for outlook.com and some secondary domains, but not for microsoft.com. Of course, the issue also occurs with mailto:email address removed for privacy reasons and other IP addresses, so this is an example. It started to occur around two weeks ago, not sure if the provider changed policies or Microsoft changed the whitelisting; of course the provider refuses to overrun dnswl.org it, e.g. by own whitelisting. Who at Microsoft could I ask to fix that kind of issues? I don't find any appropriate category in their support menues, M365 support says the cannot help (TrackingID#2603031420001611). Thanks in advance for any hints, this is my first posting here, so please forgive me, if this is a dumb question.
Can we hide default address lists in Outlook Address Book and show only custom ones?
There are existing Custom Address Lists. When users use the MS Outlook App (Office 2019) and open the Address Book, is it possible to hide the other address lists (including domain-sg-GAL, Global Address List, and domain-sg-Rooms), and only display the Custom Address Lists (domain-HK-AL and domain-sg-AL) — the ones shown in green in the photo?Cross Tenant Migration licensing
Hello, I'm planning a native cross-tenant migration for several shared mailboxes that have archives enabled. I’m looking to confirm if it is necessary to temporarily convert these to user mailboxes in the source to ensure the archive data migrates successfully. Also, what specific licenses should I assign to the target objects specifically, do I need to provide an Exchange Online Plan 2 plus the Cross-Tenant User Data Migration add-on for each shared mailbox? If anyone has handled archived shared mailboxes recently, I’d appreciate a quick confirmation on the cleanest licensing and conversion steps. Thank you in advance ! :)
550 5.7.705 Tenant Email Block 55+ Hours - Support Unresolved
Our M365 tenant (labaradorpake.onmicrosoft.com) has been blocked from sending outbound email for over 55 hours with error 550 5.7.705 Access denied, tenant has exceeded threshold. Despite multiple support tickets and promises of 24-hour resolution, the block remains active. **Error Details:** - NDR: 550 5.7.705 Access denied, tenant has exceeded threshold - Scope: External outbound email only is blocked; internal tenant-to-tenant email works fine - Microsoft Defender Restricted Entities page shows 0 restricted users — the block is at tenant level, NOT user level - No transport rules exist that could be blocking outbound - No alerts in Exchange Admin Center **Timeline:** - June 19: Support ticket #2606190040005588 created, agent Manisha confirmed remediation complete and promised block would be lifted within 24 hours - June 21 (55+ hours later): Block STILL ACTIVE. Manisha has not responded to follow-ups. - June 21: Created 2nd ticket #2606210040000778, assigned to agent Odunayo — no action taken - June 21: Created 3rd ticket #2606210040000844 with phone callback request — no callback received yet **What we have tried:** 1. Three Microsoft support tickets (all Sev C) 2. Escalation emails to agent, tech lead, team manager (all bounce due to tenant block preventing outbound email) 3. Support Assistant chat bot — cannot escalate to human agents 4. Azure Portal support — No Access for this tenant tier 5. getsupport.microsoft.com — No Access 6. Microsoft Learn Q&A post: https://learn.microsoft.com/en-us/answers/questions/5926147 7. Phone callback requested on 3rd ticket — still waiting **Critical Impact:** The tenant cannot send ANY external email. All outbound messages to external recipients bounce with 550 5.7.705. This is a complete business email outage that has persisted for over 55 hours despite Microsoft support confirming remediation was complete. Has anyone experienced a similar tenant-level block (550 5.7.705) that took this long to resolve? What escalation paths actually work when support agents are unresponsive? Any advice on getting this block lifted urgently would be greatly appreciated. Cross-posted from Microsoft Learn Q&A: https://learn.microsoft.com/en-us/answers/questions/5926147
