What is the best way to handle networking during a long-running cloud migration?
Hi everyone, I'd like to get some opinions from people who have worked on large-scale cloud migrations. Consider a migration where workloads are gradually moved from AWS to Azure over several weeks or months rather than being migrated in a single cutover. During the migration period, both environments need to remain operational. A simplified architecture could look like: AWS workloads | | Existing connectivity | AWS Network | | Inter-cloud connectivity | Azure Network | | Azure workloads The challenge is that applications may temporarily become distributed across both clouds. For example: • Application servers may still be running in AWS. • New application components may already be deployed in Azure. • Databases or shared services may remain in AWS temporarily. • DNS and routing may need to support both environments. • Migration tools may require connectivity to source and target environments. • Some workloads may be migrated much earlier than their dependent services. For a long-running migration like this, what architecture would you recommend? Some options I have been considering are: 1. Site-to-site VPN between AWS and Azure 2. Dedicated connectivity such as AWS Direct Connect + Azure ExpressRoute 3. A combination of dedicated connectivity and VPN for backup 4. A hub-and-spoke architecture in Azure with controlled connectivity back to AWS 5. Application-level connectivity rather than relying heavily on network-level connectivity Another question is how you would handle routing. Would you prefer to: • Keep AWS and Azure routing domains mostly independent? • Use a centralized hub for cross-cloud traffic? • Advertise routes dynamically using BGP? • Restrict cross-cloud communication to only the application dependencies that require it? For a migration lasting several months, what approach have you found to be the most reliable and easiest to operate? I'm particularly interested in lessons learned around: • Routing • DNS • Security • Latency • Failover • Monitoring • Avoiding unexpected cross-cloud traffic costs Would appreciate experiences from anyone who has handled a production AWS-to-Azure or Azure-to-AWS migration.Issue with gMSA when installing Cloud Sync
We are trying to install Cloud Sync to make use of the group writeback. However, we get the same error message every time we try to complete the installation We already tried: created a new sync server from scratch test the service account with "test-ADServiceAccount" check the encryption settings of the GMSA (the account is being created in the AD) removed an old orphaned GC tried it with a custom GMSA (same error) gave the server access to the GMSA via set-ADServiceAccount Did anyone else ever had this problem or know how to fix it?Applying DevOps Principles on Lean Infrastructure. Lessons From Scaling to 102K Users.
Hi Azure Community, I'm a Microsoft Certified DevOps Engineer, and I want to share an unusual journey. I have been applying DevOps principles on traditional VPS infrastructure to scale to 102,000 users with 99.2% uptime. Why am I posting this in an Azure community? Because I'm planning migration to Azure in 2026, and I want to understand: What mistakes am I already making that will bite me during migration? THE CURRENT SETUP Platform: Social commerce (West Africa) Users: 102,000 active Monthly events: 2 million Uptime: 99.2% Infrastructure: Single VPS Stack: PHP/Laravel, MySQL, Redis Yes - one VPS. No cloud. No Kubernetes. No microservices. WHY I HAVEN'T USED AZURE YET Honest answer: Budget constraints in emerging market startup ecosystem. At our current scale, fully managed Azure services would significantly increase monthly burn before product-market expansion. The funding we raised needs to last through growth milestones. The trade: I manually optimize what Azure would auto-scale. I debug what Application Insights would catch. I do by hand what Azure Functions would automate. DEVOPS PRACTICES THAT KEPT US RUNNING Even on single-server infrastructure, core DevOps principles still apply: CI/CD Pipeline (GitHub Actions) • 3-5 deployments weekly • Zero-downtime deploys • Automated rollback on health check failures • Feature flags for gradual rollouts Monitoring & Observability • Custom monitoring (would love Application Insights) • Real-time alerting • Performance tracking and slow query detection • Resource usage monitoring Automation • Automated backups • Automated database optimization • Automated image compression • Automated security updates Infrastructure as Code • Configs in Git • Deployment scripts • Environment variables • Documented procedures Testing & Quality • Automated test suite • Pre-deployment health checks • Staging environment • Post-deployment verification KEY OPTIMIZATIONS Async Job Processing • Upload endpoint: 8 seconds → 340ms • 4x capacity increase Database Optimization • Feed loading: 6.4 seconds → 280ms • Strategic caching • Batch processing Image Compression • 3-8MB → 180KB (94% reduction) • Critical for mobile users Caching Strategy • Redis for hot data • Query result caching • Smart invalidation Progressive Enhancement • Server-rendered pages • 2-3 second loads on 4G WHAT I'M WORRIED ABOUT FOR AZURE MIGRATION This is where I need your help: Architecture Decisions • App Service vs Functions + managed services? • MySQL vs Azure SQL? • When does cost/benefit flip for managed services? Cost Management • How do startups manage Azure costs during growth? • Reserved instances vs pay-as-you-go? • Which Azure services are worth the premium? Migration Strategy • Lift-and-shift first, or re-architect immediately? • Zero-downtime migration with 102K active users? • Validation approach before full cutover? Monitoring & DevOps • Application Insights - worth it from day one? • Azure DevOps vs GitHub Actions for Azure deployments? • Operational burden reduction with managed services? Development Workflow • Local development against Azure services? • Cost-effective staging environments? • Testing Azure features without constant bills? MY PLANNED MIGRATION PATH Phase 1: Hybrid (Q1 2026) • Azure CDN for static assets • Azure Blob Storage for images • Application Insights trial • Keep compute on VPS Phase 2: Compute Migration (Q2 2026) • App Service for API • Azure Database for MySQL • Azure Cache for Redis • VPS for background jobs Phase 3: Full Azure (Q3 2026) • Azure Functions for processing • Full managed services • Retire VPS QUESTIONS FOR THIS COMMUNITY Question 1: Am I making migration harder by waiting? Should I have started with Azure at higher cost to avoid technical debt? Question 2: What will break when I migrate? What works on VPS but fails in cloud? What assumptions won't hold? Question 3: How do I validate before cutting over? Parallel infrastructure? Gradual traffic shift? Safe patterns? Question 4: Cost optimization from day one? What to optimize immediately vs later? Common cost mistakes? Question 5: DevOps practices that transfer? What stays the same? What needs rethinking for cloud-native? THE BIGGER QUESTION Have you migrated from self-hosted to Azure? What surprised you? I know my setup isn't best practice by Azure standards. But it's working, and I've learned optimization, monitoring, and DevOps fundamentals in practice. Will those lessons transfer? Or am I building habits that cloud will expose as problematic? Looking forward to insights from folks who've made similar migrations. --- About the Author: Microsoft Certified DevOps Engineer and Azure Developer. CTO at social commerce platform scaling in West Africa. Preparing for phased Azure migration in 2026. P.S. I got the Azure certifications to prepare for this migration. Now I need real-world wisdom from people who've actually done it!
Azure automation feature, improvements and bugs
This is by no means meant as critic as i love the Azure Automation Account product and its current features but these are thing that i would love to see as an offering/fixed for the future. Source Control (I can only speak for Github as that is what i use): Bugs: Tags being overwritten / removed by source controll both on full sync but also on incremential syncs (Already reported in case #2508010040002105) Features: Runbooks in source control is not being deleted in automation account when they have been deleted in source control. Support for diffrent sync types other than PowerShell 5.1 (Personally we will not consider upgrading to a newer version before there is source control implemented) Support for syncing the full repository instead of only a specific folder. So recursive source control for easier organisation in repositories I know we can setup multiple source control in azure automation but that seems a bit redundant and more maintance as the source control integration expires after 1 year does not matter if your PAT token is set to never expires Add support for syncing synopsis / description for at least PowerShell scripts so it grabs it directly from the given script and inputs it into the description field. Just the output of get-help .\ScriptName.ps1 Logging: Bugs: From time to time we see that logs is being displayed twice after each other so lets say you get the first result of logs. For this example lets say the first 10 entries in the All log page and scroll down further then the same 10 entries are repeated again and again and again this can also be seen by the time stamp of the log entry. (No new network requests for logs is being made so i believe this might be a bug in a javascript without being 100% certain) The most often time we see this bug is when a runbook is still running so it might be the log output stream that messes this up. And just to provide a picture for refrence without exposing anything sensitive the bug can be seen based on timestamps here: PowerShell 7 and above log outputs seems to contain some non escaped ASCI characters which makes the logs harder to read and also makes a log object being split into multiple log entries in Azure automation Log outputs Seems to have been fixed since i last tested Features: Searching for a specific job id in the general job list. Currently there is a work arround by going into a specific runbook - go to jobs - Press "Find job" and then you can lookup a jobid globally but the UI is not being updated correctly as displayed here: Would love to see a button here or be able to search for a jobid Formatting log outputs so you can do multi line output in a single log output entry E.G. "Write-output "New´r´nLine" So the output entry contains multiple lines for easier human readable log outputs Runbook page: Bugs: Searching for runbook names seems a bit buggy as far as i have seen there is 3 diffrent results for the end user Base image intialy looking at all runbooks One option is that it is not able to find a runbook with that name I have not been able to replicate it to get a picture of it. Another is that it displays a list of runbooks none of which matches what you searched for Third is that when you have searched for something and remove your search it does not return the original view Features: Ability to go to a previous job and re-run it/restart it with the same parameters. Think a bit like the way you can restart a github action run Scheduling: Features: More of a feature request but adding the schedule for a runbook directly in the code is awesome. (This is something we currently do by adding a parameter that contains the scheduling information then we have a runbook going over all our runbooks every hour and looking for this parameter and then constructing a schedule if it does not exist and links the runbook to the schedule and finally we also add a tag mentioning If the schedule name is enabled or not (*back to the issue in source control removing the tag*)) Hybrid workers: Features: I personally would love the ability to pause a hybrid worker in a hybrid worker group - Why? - Well we currently have 4 hybrid workers all running windows and have monthly patch windows and if a job hits a hybrid worker that is in patch then the jobs would go into a suspended state and not be picked up again Now we could remove the hybrid worker from the group but that would also remove the extension which would be reinstalled when added and then we would hit this https://learn.microsoft.com/en-us/azure/automation/troubleshoot/extension-based-hybrid-runbook-worker#scenario-runbooks-go-into-a-suspended-state-on-a-hybrid-runbook-worker-when-using-a-custom-account-on-a-server-with-user-account-control-uac-enabled This is an issue we originally started experiencing when we migrated from agent-based hybrid workers to extension based due to the discontinuation of agent-based. Another great reason is when needing to troubleshoot something on a specific hybrid worker or even when needing to update modules on a specific hybrid worker as this can not be done while the hybrid worker is still running jobs unless you use force or hit a time that it is not running or by manually stopping the service and then again end up with suspended jobs that is not being picked up again. Additional features that i personally would love to see as an offering: A front end for azure automation for end users (Think self-service portal) as some kind of add-on feature allowing a specific group of people to start a given runbook but supplying a more user friendly front end for it while also including some more limitations for end user groupings. I know there is already third party solutions for this and tbh I almost created one my self on my last maternity leave but my company chose not to pursue it further as the statement is we have 1 self service platform being servicenow can be viewed https://github.com/Mynster9361/Self-Service-Frontend-Azure-Automation just to give some inspiration if needed RBAC permissions for individual runbooks (as far as i remember this can already be done through cli) A General overview management blade for managing webhooks and the associated runbooks Currently there is no way to know which runbooks has an active / inactive webhook assigned to them as the only way to see this is by going to a runbook go to the webhooks blade and look if there is one or not. Personally i would love to see a blade on the general overview called "Webhooks" that looks similar to this table maybe: RunbookNameExpirationLast triggeredStatusRunbook1 (Clickable to get directly to the runbook)Custom_name_for_this webhook02/01/2022 16:00 EnabledRunbook2webhook211/11/2026 16:00TodayDisabledRunbook3webhook311/11/2027 16:00TodayEnabled Instead of webhook being a gentleman agreemnet on when you can enable and when you shouldn't enable and naming and such you have 1 general overview of all webhooks which would give value in regards to security and easier management of webhooks The things i see as most critical or highest on my wish list: To list 2 things i would like to see sooner rather than later Source control definitely needs to be updated/revamped so it both supports other languages/versions and also does not remove tags. Another thing that would be nice to have is to force it to follow source control so if i delete something that is in source control it is also deleted in azure automation Hybrid workers in maintenance mode so it completes running jobs and you are able to work on the hybrid worker whether it be bugs or just regular updates.Custom Windows Server Standard VM on Azure: It Works, But Is It Licensing Compliant?
Hi everyone, I wanted to share a recent technical experience where I successfully created and deployed a Windows Server Standard VM on Azure using a fully custom image. I started by downloading the official Windows Server Standard Evaluation ISO. I created a Generation 2 VM in Hyper-V and completed the OS setup using the Desktop Experience edition. Once the configuration was done, I ran sysprep to generalize the image. After that, I converted the disk from VHDX to VHD in fixed format, which turned out to be a critical step because Azure does not accept dynamic disks. The resulting file was around 127 GB, so I uploaded it to a premium storage account container to ensure performance. From there, I created a Generation 2 image in Azure and deployed a new VM from it. I then activated the Standard edition with a valid product key. Everything worked smoothly, but I’m still unsure whether this method is fully compliant with Microsoft’s licensing policies. Specifically, I’m trying to understand if going from an Evaluation ISO to sysprep, upload, deployment, and activation in Azure is a valid and compliant scenario when not using BYOL with Software Assurance or a CSP license. Has anyone gone through this process or has any insights on the compliance aspect? Thanks in advance for any guidance or clarification.Mine your Azure backup data, it could save you 💰💡
Your data has a story to tell. Mine it, decipher it, and turn it into actionable outcomes. 📊🔍 Azure backups can become orphaned in several ways (I'll dive into that in a future post). But here’s a key point: orphaned doesn’t always mean useless, hence the word “Potential” in the title of my Power BI report. Each workload needs to be assessed individually. If a backup is no longer needed, you might be paying for it - unnecessarily and unknowingly. 🕵️♂️💸 To uncover these hidden costs, I combined data from the Azure Business Continuity Center with a PowerShell script I wrote to extract LastBackupTime and other metadata. This forms the foundation of my report, helping visualize and track backup usage over time. This approach helped me identify forgotten one-time backups, VMs deleted without stopping the backup, workloads excluded due to policy changes, and backups left behind after resource migrations. If you delete unneeded backups and have soft-delete enabled, the backup size drops to zero and Azure stops charging for it. ✅🧹 💡 Do your Azure backups have their own untold story to tell? 📸 Here's a snapshot of my report that helped me uncover these insights 👇
Scaling Smart with Azure: Architecture That Works
Hi Tech Community! I’m Zainab, currently based in Abu Dhabi and serving as Vice President of Finance & HR at Hoddz Trends LLC a global tech solutions company headquartered in Arkansas, USA. While I lead on strategy, people, and financials, I also roll up my sleeves when it comes to tech innovation. In this discussion, I want to explore the real-world challenges of scaling systems with Microsoft Azure. From choosing the right architecture to optimizing performance and cost, I’ll be sharing insights drawn from experience and I’d love to hear yours too. Whether you're building from scratch, migrating legacy systems, or refining deployments, let’s talk about what actually works.Comparision on Azure Cloud Sync and Traditional Entra connect Sync.
Introduction In the evolving landscape of identity management, organizations face a critical decision when integrating their on-premises Active Directory (AD) with Microsoft Entra ID (formerly Azure AD). Two primary tools are available for this synchronization: Traditional Entra Connect Sync (formerly Azure AD Connect) Azure Cloud Sync While both serve the same fundamental purpose, bridging on-prem AD with cloud identity, they differ significantly in architecture, capabilities, and ideal use cases. Architecture & Setup Entra Connect Sync is a heavyweight solution. It installs a full synchronization engine on a Windows Server, often backed by SQL Server. This setup gives administrators deep control over sync rules, attribute flows, and filtering. Azure Cloud Sync, on the other hand, is lightweight. It uses a cloud-managed agent installed on-premises, removing the need for SQL Server or complex infrastructure. The agent communicates with Microsoft Entra ID, and most configurations are handled in the cloud portal. For organizations with complex hybrid setups (e.g., Exchange hybrid, device management), is Cloud Sync too limited?
🔥 Hybrid Networking 101: Linking On-Prem to Azure 🔥
Many organizations seek to extend their networks to include subnets and virtual machines (VMs) hosted on Azure. The goal is to enable seamless connectivity between on-premises computers in a data center and Azure-based virtual machines. 🔹 Common Use Cases for Hybrid Networking: # Application Connectivity: You have an Azure-hosted application that needs access to your on-premises database servers. # Branch Office Integration: Your business operates retail stores worldwide and requires a single centralized service to connect all locations. # Remote Access: You need secure remote access to your Azure VMs and applications. # Data Synchronization: You want to connect on-premises servers with Azure servers for real-time synchronization and data transfer. # To address these scenarios, Azure provides four key networking solutions: ✅ Point-to-Site VPN (P2S) ✅ Site-to-Site VPN (S2S) ✅ ExpressRoute ✅ Azure Virtual WAN One essential component that supports all these solutions is Azure VPN Gateway. Let's explore its capabilities! 🔍 🚀 Azure VPN Gateway 🚀 # Secure Connectivity Between Azure & On-Premises by encrypting data while transferring it between Azure VNets and on-premises servers over the internet. # Multiple connections can be established using a single VPN Gateway, sharing available bandwidth across all VPN tunnels. # The gateway consists of Azure-managed VMs, automatically deployed and configured in a GatewaySubnet with a CIDR size of /27. # There are two types of gateways: 🔹 VPN Gateway (for encrypted connections) 🔹 ExpressRoute Gateway (for dedicated high-speed connectivity) 💡 Gateway SKUs define performance characteristics, including: # Supported tunnel types (S2S, P2S, VNet-to-VNet) # Maximum aggregate throughput # BGP (Border Gateway Protocol) support # Scalability options (resize within the same generation and family via Azure Portal or PowerShell) 🚀 VPN Gateway Types: # Route-Based VPN: Supports S2S & P2S connections—widely used in hybrid networking. # Policy-Based VPN: Limited to Basic SKUs and allows only S2S connections (not ideal for Remote Access). 🔹 Local Network Gateway: Represents your on-premises router or firewall, enabling Azure to recognize your internal network's public IP and subnets for connectivity via IPSec IKEv1/2. 🔹 Azure Availability Zones can be leveraged for high availability and service continuity. 📌 Point-to-Site VPN (P2S) 📌 🔹 Secure access for individual users connecting remotely to Azure VNets. 🔹 Supported protocols: OpenVPN® (SSL/TLS-based; compatible with Windows, Mac, Linux, Android, iOS) SSTP (TLS-based; Windows-only) IKEv2 (IPsec VPN solution; Mac-supported) 🔹 Authentication Methods: (1) Certificate Authentication (requires client certificates issued from a trusted root certificate). (2) Azure AD Authentication (available for OpenVPN clients). (3) Active Directory Domain Server Authentication (via RADIUS server integration). 📌 Site-to-Site VPN (S2S) 📌 🔹 Enables on-premises data centers to connect with Azure VNets via IPSec IKEv1/2. 🔹 Supports VNet-to-VNet connections over Microsoft's backbone network. 🔹 Compatible with hardware devices from vendors such as Cisco, Fortinet, Barracuda, Check Point. 🔹 Supports software VPN devices, including Microsoft RRAS and Linux Openswan. 🔹 Enables dynamic routing via BGP to propagate network changes automatically. 📌 ExpressRoute 📌 🔹 Dedicated high-speed connectivity to Microsoft Cloud (Azure, Microsoft 365). 🔹 Up to 100 Gbps speeds with low latency, ideal for business-critical applications. 🔹 Layer 3 connectivity, using BGP for seamless route exchange between on-premises and Azure networks. 📌 Azure Virtual WAN 📌 🔹 A scalable networking service integrating VPN, ExpressRoute, and SD-WAN solutions. 🔹 Provides branch connectivity using site-to-site VPN or private ExpressRoute connections. 🔹 Supports remote user VPN (P2S) for secure external access. 🔹 Follows hub-and-spoke architecture, ensuring full mesh connectivity across Azure regions. If you found this valuable, consider sharing so more professionals can benefit. Let's keep the conversation growing! 🚀Creating Custom Entra Connect Rules for Attribute Sync from Entra ID to Active Directory
We have successfully synced our Active Directory and Entra ID Directories using Entra Connect. We must create customized sync rules to force-write user attributes from Entra ID to Active Directory. This requirement is critical for integration with our HR application, DarwinBox. Since we use Exchange Online and other Microsoft 365 products, all user attributes are already populated in Entra ID. Consequently, Entra ID must be our main directory service. Could you please provide guidance on creating these custom rules in Entra Connect? Any insights or best practices would be greatly appreciated. Thank you so much.
