So, this was a total mess to upgrade and I will postpone this until maybe some minor releases for Spring Boot 4.0
Things which did not work out as expected:

jackson2 > jackson3 migration is wild. There is a openrewrite rule for this. Add this block to the plugins in the pom.xml and execute then mvn rewrite:run

            <plugin>
                <groupId>org.openrewrite.maven</groupId>
                <artifactId>rewrite-maven-plugin</artifactId>
                <version>6.34.0</version>
                <configuration>
                    <activeRecipes>
                        <recipe>org.openrewrite.java.jackson.UpgradeJackson_2_3</recipe>
                    </activeRecipes>
                </configuration>
                <dependencies>
                    <dependency>
                        <groupId>org.openrewrite.recipe</groupId>
                        <artifactId>rewrite-jackson</artifactId>
                        <version>1.19.3</version>
                    </dependency>
                </dependencies>
            </plugin>

This brings it mostly to a compileable state. But then the issue really starts, the RedisQueueService cant deserialize messages, the GoogleImporters fail because there is stuff to do when parsing the Records.json in a stream.

next problem I faced, @CacheEvict in combination with @Transaction does not work as in 3.5 anymore and the cache entries seem to be evicted asynchronous. That was not the case in the 3.5 release.

The final verdict is:
I will do it when the pressure gets higher which is in June 2026 when Spring Boot 3.5 reaches EOL

Uh oh!

[Feature Request] update to spring boot 4.0 #814

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