SharePoint 2019 to SharePoint Subscription Edition (SE) Upgrade – Major Challenges

 

SharePoint 2019 to SharePoint Subscription Edition (SE)

 Upgrade – Major Challenges

First, remember an important interview point:

✅ SharePoint 2019 → SharePoint SE is NOT an in-place upgrade.

✅ Microsoft supports the Database Attach Upgrade method. You build a new SPSE farm, copy databases, and attach them to the new farm. (Microsoft Learn)

 

High-Level Upgrade Flow

SP2019 Farm
     |
     | Backup Databases
     V
SQL Restore
     |
     V
New SPSE Farm
     |
     | Mount Databases
     V
Upgrade Content
     |
     V
Validate Sites

 

Top 15 Real-Time Challenges

1. Missing Custom Solutions (WSPs)

Problem

Many organizations have:

• Custom Web Parts
• Custom Features
• Custom Site Definitions
• Farm Solutions

When content databases are mounted, SPSE expects these components to exist.

If missing:

Test-SPContentDatabase

Shows:

Missing Feature
Missing Setup File
Missing Web Part

This is one of the most common upgrade blockers. Microsoft specifically recommends reinstalling all customizations before attaching content databases. (Microsoft Learn)

Real-Time RCA

Developer left company years ago.

Source code unavailable.

Feature IDs exist in database but solution package no longer exists.

Resolution

• Inventory all custom solutions.
• Rebuild unsupported code.
• Remove orphaned features.

 

2. Large Content Database Size

Problem

Many environments contain:

500 GB
1 TB
2 TB+

databases.

Upgrade duration becomes very long.

Challenges

• SQL backup time
• Restore time
• Mount time
• Validation time

Resolution

Split large databases before migration.

 

3. Search Service Migration

Problem

Search topology changes.

Search databases cannot simply be copied and assumed healthy.

Common Issues

• Crawl failures
• Index corruption
• Missing content sources

Resolution

Most organizations rebuild Search after migration.

 

4. Service Application Compatibility

Supported service application databases include:

• Managed Metadata
• Search
• User Profile
• Secure Store
• BDC

But configuration mismatches can create failures. (Microsoft Learn)

Real-Time Issue

Managed Metadata database attached.

Term Store inaccessible.

Cause:

Service account permission mismatch.

 

5. Authentication Issues

Problem

Old farms often use:

NTLM
Classic Mode
Kerberos

SPSE primarily uses Claims Authentication.

Symptoms

• Login failures
• Access denied
• Broken People Picker

Resolution

Plan authentication migration carefully.

 

6. Alternate Access Mapping (AAM) Problems

Problem

URLs change during migration.

Example:

Old:
http://portal.company.com

New:
https://portal.company.com

Impact

• Broken bookmarks
• Office integration issues
• Workflow failures

Microsoft recommends recreating the same URLs whenever possible. (Microsoft Learn)

 

7. Workflow Failures

Problem

Organizations commonly use:

• SharePoint 2010 Workflows
• SharePoint 2013 Workflows
• Nintex
• K2

Issues

After migration:

Workflow Suspended
Workflow Failed
Workflow Not Found

Resolution

Inventory workflows before migration.

 

8. InfoPath Forms

Problem

Many legacy environments use:

InfoPath Forms

Issues

• Missing templates
• Missing data connections
• Browser form rendering failures

Microsoft specifically highlights migrating InfoPath templates and connections. (Microsoft Learn)

 

9. SQL Version Challenges

Problem

Old environment may use:

SQL 2016
SQL 2017

New environment:

SQL 2022

Issues

• Compatibility mode
• Performance changes
• Database upgrade warnings

 

10. User Profile Synchronization

Problem

User Profile Service often breaks.

Common Symptoms

No profile photo
No manager hierarchy
No audience targeting

Resolution

Reconfigure profile synchronization.

 

11. Third-Party Product Compatibility

Examples

• Nintex
• K2
• AvePoint
• Bamboo
• Metalogix
• DocAve

Problem

Older versions may not support SPSE.

Resolution

Upgrade third-party products first.

 

12. MinRole Architecture Changes

Problem

SP2019 farms may not follow MinRole.

SPSE farms often use:

Front-End
Application
Search
Distributed Cache

Challenge

Server roles need redesign.

 

13. Performance Degradation After Upgrade

Symptoms

Slow Site Collection
Slow Search
Slow Page Load

Root Causes

• Missing indexes
• SQL memory allocation
• Search rebuild
• Cache warming

Resolution

Perform performance testing before production cutover.

 

14. Security and Permission Issues

Problem

Broken inheritance often surfaces after migration.

Examples

Access Denied
Missing Permissions
Broken Groups

Resolution

Audit:

Get-SPUser
Get-SPGroup

before migration.

 

15. Downtime and Cutover Planning

Biggest Enterprise Challenge

Business asks:

"Can we migrate with zero downtime?"

Reality:

Database Backup
Restore
Validation
DNS Switch

requires a maintenance window.

Common Strategy

1. Freeze Content
2. Read-Only Mode
3. Backup Databases
4. Restore Databases
5. Mount Content
6. Validate
7. DNS Cutover

Microsoft's documented process includes placing the old farm in read-only mode while the new SPSE farm is upgraded. (Microsoft Learn)

 

Interview Question

Q: What is the biggest challenge during SP2019 → SPSE migration?

Answer:

"The biggest challenge is identifying and validating all customizations before attaching content databases. In my experience, missing WSP solutions, custom web parts, workflow dependencies, authentication changes, and third-party integrations are the most common causes of upgrade failures. I always run Test-SPContentDatabase, inventory all custom components, validate service applications, and perform multiple test migrations before the production cutover." (Microsoft Learn)

 

Real-Time Project Migration Checklist

Pre-Migration

• Inventory farm solutions
• Inventory workflows
• Inventory service applications
• Validate SQL health
• Run Test-SPContentDatabase
• Verify third-party products
• Document AAM URLs

Migration

• Build SPSE farm
• Install custom solutions
• Restore databases
• Attach service app databases
• Mount content databases

Post-Migration

• Validate sites
• Validate Search
• Validate User Profiles
• Validate Workflows
• Performance testing
• Security testing
• Business UAT
• DNS cutover

These are the areas most frequently discussed in senior SharePoint Administrator, SharePoint Architect, and SharePoint Migration Lead interviews.

 

From <https://chatgpt.com/c/6a13c835-b558-8321-9678-3f95678f6f56>