This blog dissects common challenges organizations face during AWS migration and offers practical fixes to avoid disruptions, optimize costs, and ensure long-term scalability and success.

Migrating to AWS isn’t just a technical move—it’s a strategic leap. Whether you’re coming from on-premise infrastructure or moving from another cloud, the transition can be as exciting as it is complex. The idea of more scalability, automation, and resilience is incredibly appealing—until you hit your first “surprise” bill or spend three days debugging a security group misconfiguration.

That’s the reality many organizations face: AWS migration comes with incredible promise, but also a fair share of hiccups. The good news? You’re not alone, and most of these challenges have already been solved—sometimes creatively, sometimes painfully—by those who’ve gone before you.

This blog is your insider’s guide to common migration roadblocks, why they happen, and how to fix them without losing your sanity (or your budget). From hidden costs and compliance issues to data loss scares and underestimated timelines—we’ll walk you through real examples and expert-backed solutions.

“A smooth cloud migration is 90% preparation, 10% prayer.” — Cloud Architect Wisdom

You’ll also learn how platforms like Proso Marketplace can match you with AWS migration experts who’ve tackled these exact issues. Let’s make sure your move to the cloud doesn’t become an episode of “Cloud Nightmares.”

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1. Challenge: Unexpected Cloud Costs

• Problem: Cloud bills skyrocket due to poorly sized instances, idle resources, or unnecessary services.
• Fix:
  • Use the AWS Pricing Calculator before migrating.
  • Monitor spending with AWS Cost Explorer.
  • Adopt Reserved Instances for predictable workloads.
  • Set up budget alerts and use tagging to track spending by department.

2. Challenge: Downtime During Migration

• Problem: Business operations are interrupted due to improper cutover planning.
• Fix:
  • Use AWS Application Migration Service (MGN) for near-zero downtime moves.
  • Run pilot tests with non-critical workloads.
  • Plan your cutover during off-peak hours with rollback options.

3. Challenge: Data Transfer Bottlenecks

• Problem: Moving large datasets to AWS causes network congestion or extended timelines.
• Fix:
  • Use AWS Snowball for petabyte-scale transfers.
  • Compress data and use multipart uploads with S3.
  • Schedule uploads during non-business hours to reduce throttling.

4. Challenge: Application Compatibility Issues

• Problem: Legacy apps don’t play nicely with AWS services or Linux-based environments.
• Fix:
  • Assess with AWS Migration Evaluator.
  • Refactor or containerize legacy workloads for easier migration.
  • Use Amazon EC2 Windows instances if full refactoring isn’t feasible.

5. Challenge: Skill Gaps in Team

• Problem: Team lacks AWS knowledge, causing delays and misconfigurations.
• Fix:
  • Provide AWS training via AWS Skill Builder.
  • Hire short-term certified experts from platforms like Proso (details below).
  • Start with managed services like RDS, ECS Fargate to ease complexity.

6. Challenge: Security Misconfigurations

• Problem: Poorly configured IAM roles, security groups, or lack of encryption opens vulnerabilities.
• Fix:
  • Use the AWS Well-Architected Tool to scan for issues.
  • Enable encryption for data at rest and in transit.
  • Follow the principle of least privilege in IAM policies.
  • Set up alerts with Amazon GuardDuty.

7. Challenge: Compliance & Governance Hurdles

• Problem: Industry regulations (HIPAA, GDPR, etc.) complicate migration.
• Fix:
  • Use AWS Artifact for compliance documentation.
  • Implement tagging policies, audit trails, and log retention using CloudTrail.
  • Map data residency and encryption requirements before moving workloads.

8. Challenge: Integration Failures Post-Migration

• Problem: Apps break due to network misconfigurations or broken dependencies.
• Fix:
  • Set up VPC peering and private endpoints for service communication.
  • Use Route 53 with health checks and failover routing.
  • Maintain pre- and post-migration integration testing checklists.

9. Challenge: Underestimating Time & Scope

• Problem: Migration takes longer than expected, affecting deadlines and user experience.
• Fix:
  • Break down the migration into phases: lift-and-shift → refactor → optimize.
  • Use agile sprints to handle pieces incrementally.
  • Don’t move everything—some workloads may perform better hybrid.

10. Challenge: Post-Migration Monitoring is Weak

• Problem: Performance dips, and nobody notices until it’s too late.
• Fix:
  • Implement observability with CloudWatch and X-Ray.
  • Set up cost alerts, error alerts, and latency tracking.
  • Automate reporting for business stakeholders.

Bonus Data to Know Before You Migrate

• 📉 40% of cloud migrations exceed their initial budget estimates (Flexera Cloud Report).
• 🔄 60% of orgs experience downtime due to insufficient migration planning.
• 💡 Companies with trained teams complete migrations 35% faster than those that don’t.
• 🔒 Security misconfigurations are responsible for 75% of AWS-related data leaks.
• 🧠 Organizations that hire AWS experts externally see a 45% reduction in migration issues.
• 🛠️ 75% of post-migration success depends on optimization, not just initial deployment.

Handy Tools & Docs You’ll Need

• AWS Migration Hub
• Cloud Adoption Readiness Tool (CART)
• AWS Trusted Advisor
• AWS CloudEndure Migration

Proso Marketplace Section

Let’s be honest—AWS migration is a big job. Doing it alone is like assembling IKEA furniture without the instructions… in the dark. But the good news? You don’t have to.

Meet Proso Marketplace, a smart platform that connects you with cloud migration pros who’ve already tackled dozens of AWS transitions—successfully.

Here’s a real-world tale:
A retail SaaS firm was struggling to move from a legacy data center to AWS. They underestimated their data volume and hit a wall during testing. Through Proso, they hired a migration engineer with deep AWS Application Migration Service experience. Within two weeks, the migration was complete, and their app performance improved by 40% post-move.

Proso makes finding trusted experts ridiculously easy:

• Post your challenge (e.g., “Help me move my MongoDB to AWS”).
• Review proposals from certified experts.
• Hire the right one and get it done.

Whether you're stuck with S3 bucket policies, IAM spaghetti, or scaling issues—Proso has someone who’s seen it before and fixed it fast.

No long-term contracts. No guessing games. Just results.

👉 Visit Proso Marketplace and find the help you need—without breaking the cloud (or your budget).

Conclusion & Future Outlook

AWS migration can feel overwhelming, especially when every step forward risks setting off a domino of issues. But with the right planning, support, and mindset, it becomes a powerful springboard into a more agile, cost-effective, and innovative infrastructure.

The future of AWS migration lies in automation and intelligence. Expect more tools like AWS Application Composer and predictive resource sizing with AI to make migration smoother and less error-prone. Serverless adoption will also rise, reducing the burden of post-migration management and scaling. With observability becoming a top priority, real-time analytics and anomaly detection will be baked into the migration process itself.

But all that said—no tool can replace human experience.

So what can you do now?

• Review your current infrastructure and identify what’s holding you back.
• Use this blog as a living checklist—bookmark it, share it, and revisit during planning and execution.
• Consider Proso Marketplace if you need hands-on support from experts who’ve been in the trenches.
• Monitor this space—we’ll update it with real case studies, migration metrics, and newly released AWS tools as they drop.

The cloud journey doesn’t end at migration—it begins there. And your success depends on fixing issues before they turn into problems.

Make the move smart, not scary. We’ve got your back.

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