Spring Boot Servlet Application Crashes with NoServletContext resourcehandlermapping exception

I have a spring boot application which I've populated with a large data model. I was able to manually test the model & controller methods in my main class, but when I tried to tie in some security configuration classes to the app, it crashes when I try to debug it. I have tried to play around with overriding the SpringBootServletInitializer.onStartup(ServletContext servletcontext) and creating a custom WebApplicationinitializer extending AbstractAnnotationConfigDispatcherServletInitializer

but no dice. I'm happy to provide copies of any of the specific securityconfig or appconfig/dispatcherconfig classes, but they are pretty close to the Spring docs.

Are there any tips for digging into what the issue with annotations is / my specific custom classes / controllers or just a plain solution to this issue in general?

POM:

<project xmlns="http://maven.apache.org/POM/4.0.0" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xsi:schemaLocation="http://maven.apache.org/POM/4.0.0 https://maven.apache.org/xsd/maven-4.0.0.xsd">
  <modelVersion>4.0.0</modelVersion>

    <parent>
        <groupId>org.springframework.boot</groupId>
        <artifactId>spring-boot-starter-parent</artifactId>
        <version>2.7.2</version>
        <relativePath/> <!-- lookup parent from repository -->
    </parent>

<groupId>something</groupId>
<artifactId>something</artifactId>
<version>0.0.1-SNAPSHOT</version>
<packaging>war</packaging>
<name>something</name>
<url>https://something.com</url>
    
<properties>
        <project.build.sourceEncoding>UTF-8</project.build.sourceEncoding>
        <project.reporting.outputEncoding>UTF-8</project.reporting.outputEncoding>
        <java.version>18</java.version>
        <maven.compiler.source>${java.version}</maven.compiler.source>
        <maven.compiler.target>${java.version}</maven.compiler.target>
        <tomcat.version>9.0.65</tomcat.version>
        <vaadin.version>23.0.9</vaadin.version>
</properties>
    
    <dependencies>
        <dependency>
        <groupId>com.auth0</groupId>
            <artifactId>java-jwt</artifactId>
            <version>3.19.2</version>
        </dependency>
        <dependency>
            <groupId>com.fasterxml.jackson.core</groupId>
            <artifactId>jackson-databind</artifactId>
        </dependency>
        <dependency>
            <groupId>org.springframework.boot</groupId>
            <artifactId>spring-boot-starter-data-jpa</artifactId>

        </dependency>
        <dependency>
            <groupId>org.springframework.boot</groupId>
            <artifactId>spring-boot-starter-jdbc</artifactId>

        </dependency>
        <dependency>
            <groupId>org.springframework.boot</groupId>
            <artifactId>spring-boot-starter-data-rest</artifactId>

        </dependency>
        <dependency>
            <groupId>org.springframework.boot</groupId>
            <artifactId>spring-boot-starter-test</artifactId>

        </dependency>       
        <dependency>
            <groupId>org.springframework.boot</groupId>
            <artifactId>spring-boot-starter-oauth2-client</artifactId>

        </dependency>
        <dependency>
            <groupId>org.springframework.boot</groupId>
            <artifactId>spring-boot-starter-oauth2-resource-server</artifactId>

        </dependency>
        <dependency>
            <groupId>org.springframework.boot</groupId>
            <artifactId>spring-boot-starter-security</artifactId>

        </dependency>
        <dependency>
            <groupId>mysql</groupId>
            <artifactId>mysql-connector-java</artifactId>
            <scope>runtime</scope>

        </dependency>
        <dependency>
            <groupId>org.springframework.security</groupId>
            <artifactId>spring-security-test</artifactId>
            <scope>test</scope>

        </dependency>
        <dependency>
            <groupId>org.hibernate</groupId>
            <artifactId>hibernate-core</artifactId>

        </dependency>         
        <dependency>
            <groupId>org.slf4j</groupId>
            <artifactId>slf4j-api</artifactId>

        </dependency>
        <dependency>
            <groupId>org.projectlombok</groupId>
            <artifactId>lombok</artifactId>
            <scope>provided</scope>
        </dependency>   
        <dependency>
            <groupId>org.apache.httpcomponents</groupId>
            <artifactId>httpclient</artifactId>
        </dependency>
        <dependency>
            <groupId>io.jsonwebtoken</groupId>
            <artifactId>jjwt</artifactId>
            <version>0.9.0</version>
        </dependency>
        <dependency>
            <groupId>org.springframework.boot</groupId>
            <artifactId>spring-boot-starter-web</artifactId>
        </dependency>
        <dependency>
            <groupId>javax.servlet</groupId>
            <artifactId>servlet-api</artifactId>
            <version>2.5</version>
        </dependency>
        <dependency>
            <groupId>org.springframework.boot</groupId>
            <artifactId>spring-boot-configuration-processor</artifactId>
            <optional>true</optional>
        </dependency>
    </dependencies>
  <build>
    <sourceDirectory>src</sourceDirectory>
    <finalName>${project.artifactId}</finalName>
    <resources>
      <resource>
        <directory>resources</directory>
        <excludes>
          <exclude>**/*.java</exclude>
        </excludes>
      </resource>
    </resources>
    <plugins>
            <plugin>
                <groupId>org.springframework.boot</groupId>
                <artifactId>spring-boot-maven-plugin</artifactId>
            </plugin>
            <plugin>
                <groupId>com.microsoft.azure</groupId>
                <artifactId>azure-webapp-maven-plugin</artifactId>
                <version>2.5.0</version>
            </plugin>
            <plugin>
                <artifactId>maven-clean-plugin</artifactId>
                
            </plugin>
            <plugin>
                <artifactId>maven-resources-plugin</artifactId>
                <executions>
                    <execution>
                        <id>
                        copy-resources
                        </id>
                        <phase>
                        validate
                        </phase>
                        <goals>
                            <goal>copy-resources</goal>
                        </goals>
                        <configuration>
                            <outputDirectory>${basedir}/target/classes/static/</outputDirectory>
                            <resources>
                                <resource>
                                    <directory>
                                    ${basedir}/../AwesomeProject/bin
                                    </directory>
                                </resource>
                            </resources>
                        </configuration>
                    </execution>
                </executions> 
            </plugin>
            <plugin>
                <groupId>org.apache.maven.plugins</groupId>
                <artifactId>maven-war-plugin</artifactId>
                
            </plugin>
            <plugin>
                <artifactId>maven-install-plugin</artifactId>
                
            </plugin>
            <plugin>
                <artifactId>maven-deploy-plugin</artifactId>
                
            </plugin>
            <plugin>
                <groupId>org.apache.tomcat.maven</groupId>
                <artifactId>tomcat7-maven-plugin</artifactId>
                <version>2.2</version>
                <configuration>
                    <url>http://localhost:8081/</url>
                    <server>tomcatdev</server>
                    <path>/stuffid</path>
                </configuration>
            </plugin>
    </plugins>
  </build>

            
<repositories>
    <repository>
        <id>local-maven-repo</id>
        <url>file:///${project.basedir}/local-maven-repo</url>
    </repository>
</repositories>


</project>

Stack trace error:

 :42.062 ERROR 73202 - [main] o.s.boot.SpringApplication               : Application run failed

org.springframework.beans.factory.BeanCreationException: Error creating bean with name 'resourceHandlerMapping' defined in class path resource [org/springframework/boot/autoconfigure/web/servlet/WebMvcAutoConfiguration$EnableWebMvcConfiguration.class]: Bean instantiation via factory method failed; nested exception is org.springframework.beans.BeanInstantiationException: Failed to instantiate [org.springframework.web.servlet.HandlerMapping]: Factory method 'resourceHandlerMapping' threw exception; nested exception is java.lang.IllegalStateException: No ServletContext set
    at org.springframework.beans.factory.support.ConstructorResolver.instantiate(ConstructorResolver.java:658) ~[spring-beans-5.3.22.jar:5.3.22]
    at org.springframework.beans.factory.support.ConstructorResolver.instantiateUsingFactoryMethod(ConstructorResolver.java:638) ~[spring-beans-5.3.22.jar:5.3.22]
    at org.springframework.beans.factory.support.AbstractAutowireCapableBeanFactory.instantiateUsingFactoryMethod(AbstractAutowireCapableBeanFactory.java:1352) ~[spring-beans-5.3.22.jar:5.3.22]
    at org.springframework.beans.factory.support.AbstractAutowireCapableBeanFactory.createBeanInstance(AbstractAutowireCapableBeanFactory.java:1195) ~[spring-beans-5.3.22.jar:5.3.22]
    at org.springframework.beans.factory.support.AbstractAutowireCapableBeanFactory.doCreateBean(AbstractAutowireCapableBeanFactory.java:582) ~[spring-beans-5.3.22.jar:5.3.22]
    at org.springframework.beans.factory.support.AbstractAutowireCapableBeanFactory.createBean(AbstractAutowireCapableBeanFactory.java:542) ~[spring-beans-5.3.22.jar:5.3.22]
    at org.springframework.beans.factory.support.AbstractBeanFactory.lambda$doGetBean$0(AbstractBeanFactory.java:335) ~[spring-beans-5.3.22.jar:5.3.22]
    at org.springframework.beans.factory.support.DefaultSingletonBeanRegistry.getSingleton(DefaultSingletonBeanRegistry.java:234) ~[spring-beans-5.3.22.jar:5.3.22]
    at org.springframework.beans.factory.support.AbstractBeanFactory.doGetBean(AbstractBeanFactory.java:333) ~[spring-beans-5.3.22.jar:5.3.22]
    at org.springframework.beans.factory.support.AbstractBeanFactory.getBean(AbstractBeanFactory.java:208) ~[spring-beans-5.3.22.jar:5.3.22]
    at org.springframework.beans.factory.support.DefaultListableBeanFactory.preInstantiateSingletons(DefaultListableBeanFactory.java:955) ~[spring-beans-5.3.22.jar:5.3.22]
    at org.springframework.context.support.AbstractApplicationContext.finishBeanFactoryInitialization(AbstractApplicationContext.java:918) ~[spring-context-5.3.22.jar:5.3.22]
    at org.springframework.context.support.AbstractApplicationContext.refresh(AbstractApplicationContext.java:583) ~[spring-context-5.3.22.jar:5.3.22]
    at org.springframework.boot.web.servlet.context.ServletWebServerApplicationContext.refresh(ServletWebServerApplicationContext.java:147) ~[spring-boot-2.7.2.jar:2.7.2]
    at org.springframework.boot.SpringApplication.refresh(SpringApplication.java:734) ~[spring-boot-2.7.2.jar:2.7.2]
    at org.springframework.boot.SpringApplication.refreshContext(SpringApplication.java:408) ~[spring-boot-2.7.2.jar:2.7.2]
    at org.springframework.boot.SpringApplication.run(SpringApplication.java:308) ~[spring-boot-2.7.2.jar:2.7.2]
    at org.springframework.boot.SpringApplication.run(SpringApplication.java:1306) ~[spring-boot-2.7.2.jar:2.7.2]
    at org.springframework.boot.SpringApplication.run(SpringApplication.java:1295) ~[spring-boot-2.7.2.jar:2.7.2]
    at id.stuff.main.api.Application.main(Application.java:92) ~[classes/:na]
Caused by: org.springframework.beans.BeanInstantiationException: Failed to instantiate [org.springframework.web.servlet.HandlerMapping]: Factory method 'resourceHandlerMapping' threw exception; nested exception is java.lang.IllegalStateException: No ServletContext set
    at org.springframework.beans.factory.support.SimpleInstantiationStrategy.instantiate(SimpleInstantiationStrategy.java:185) ~[spring-beans-5.3.22.jar:5.3.22]
    at org.springframework.beans.factory.support.ConstructorResolver.instantiate(ConstructorResolver.java:653) ~[spring-beans-5.3.22.jar:5.3.22]
    ... 19 common frames omitted
Caused by: java.lang.IllegalStateException: No ServletContext set
    at org.springframework.util.Assert.state(Assert.java:76) ~[spring-core-5.3.22.jar:5.3.22]
    at org.springframework.web.servlet.config.annotation.WebMvcConfigurationSupport.resourceHandlerMapping(WebMvcConfigurationSupport.java:591) ~[spring-webmvc-5.3.22.jar:5.3.22]
    at java.base/jdk.internal.reflect.DirectMethodHandleAccessor.invoke(DirectMethodHandleAccessor.java:104) ~[na:na]
    at java.base/java.lang.reflect.Method.invoke(Method.java:577) ~[na:na]
    at org.springframework.beans.factory.support.SimpleInstantiationStrategy.instantiate(SimpleInstantiationStrategy.java:154) ~[spring-beans-5.3.22.jar:5.3.22]
    ... 20 common frames omitted
Disconnected from the target VM, address: '1xx', transport: 'socket'
Process finished with exit code 1