diff --git a/modules/openapi-generator/src/main/resources/JavaSpring/apiController.mustache b/modules/openapi-generator/src/main/resources/JavaSpring/apiController.mustache
index 05d90aeca4e3..7de0ac763bcf 100644
--- a/modules/openapi-generator/src/main/resources/JavaSpring/apiController.mustache
+++ b/modules/openapi-generator/src/main/resources/JavaSpring/apiController.mustache
@@ -81,11 +81,10 @@ public class {{classname}}Controller implements {{classname}} {
 {{^isDelegate}}
     {{^reactive}}
 
-    @Nullable
     private final NativeWebRequest request;
 
     @Autowired
-    public {{classname}}Controller(@Nullable NativeWebRequest request) {
+    public {{classname}}Controller(NativeWebRequest request) {
         this.request = request;
     }
 
diff --git a/modules/openapi-generator/src/test/java/org/openapitools/codegen/java/assertions/JavaFileAssert.java b/modules/openapi-generator/src/test/java/org/openapitools/codegen/java/assertions/JavaFileAssert.java
index db79fecc3128..3817c55367bf 100644
--- a/modules/openapi-generator/src/test/java/org/openapitools/codegen/java/assertions/JavaFileAssert.java
+++ b/modules/openapi-generator/src/test/java/org/openapitools/codegen/java/assertions/JavaFileAssert.java
@@ -195,7 +195,7 @@ public JavaFileAssert fileContains(final String... lines) {
                 .toString();
         Assertions.assertThat(actualBody)
                 .withFailMessage(
-                        "File should contains lines\n====\n%s\n====\nbut actually was\n====\n%s\n====",
+                        "File should contain lines\n====\n%s\n====\nbut actually was\n====\n%s\n====",
                         Arrays.stream(lines).collect(Collectors.joining(System.lineSeparator())), actualBody
                 )
                 .contains(lines);
@@ -209,7 +209,7 @@ public JavaFileAssert fileDoesNotContain(final String... lines) {
                 .toString();
         Assertions.assertThat(actualBody)
                 .withFailMessage(
-                        "File should not contains lines\n====\n%s\n====\nbut actually was\n====\n%s\n====",
+                        "File should not contain lines\n====\n%s\n====\nbut actually was\n====\n%s\n====",
                         Arrays.stream(lines).collect(Collectors.joining(System.lineSeparator())), actualBody
                 )
                 .doesNotContain(lines);
@@ -227,11 +227,25 @@ public JavaFileAssert fileContainsPattern(final String pattern) {
                 .toString();
         Assertions.assertThat(actualBody)
                 .withFailMessage(
-                        "File should contains pattern\n====\n%s\n====\nbut actually was\n====\n%s\n====",
+                        "File should contain pattern\n====\n%s\n====\nbut actually was\n====\n%s\n====",
                         pattern, actualBody
                 )
                 .containsPattern(pattern);
 
         return this;
     }
+
+    public JavaFileAssert fileDoesNotContainPattern(final String pattern) {
+        final String actualBody = actual.getTokenRange()
+                .orElseThrow(() -> new IllegalStateException("Empty file"))
+                .toString();
+        Assertions.assertThat(actualBody)
+                .withFailMessage(
+                        "File should not contain pattern\n====\n%s\n====\nbut actually was\n====\n%s\n====",
+                        pattern, actualBody
+                )
+                .doesNotContainPattern(pattern);
+
+        return this;
+    }
 }
diff --git a/modules/openapi-generator/src/test/java/org/openapitools/codegen/java/assertions/TypeAnnotationsAssert.java b/modules/openapi-generator/src/test/java/org/openapitools/codegen/java/assertions/TypeAnnotationsAssert.java
index abad31de31eb..19e013cc5d92 100644
--- a/modules/openapi-generator/src/test/java/org/openapitools/codegen/java/assertions/TypeAnnotationsAssert.java
+++ b/modules/openapi-generator/src/test/java/org/openapitools/codegen/java/assertions/TypeAnnotationsAssert.java
@@ -4,6 +4,7 @@
 import org.assertj.core.util.CanIgnoreReturnValue;
 
 import java.util.List;
+import java.util.regex.Pattern;
 
 @CanIgnoreReturnValue
 public class TypeAnnotationsAssert extends AbstractAnnotationsAssert<TypeAnnotationsAssert> {
@@ -18,4 +19,30 @@ protected TypeAnnotationsAssert(final JavaFileAssert fileAssert, final List<Anno
     public JavaFileAssert toType() {
         return fileAssert;
     }
+
+    /**
+     * assert that the annotation is not specifed in an import.
+     *
+     * @param name classname of the annotation. For example "Nullable" or a full qualified class name like "java.util.List"
+     */
+    public TypeAnnotationsAssert doesNotImportAnnotation(final String name) {
+        String pattern = "import\\s+" +
+                (name.contains(".")?"" : "[\\w.]+\\.") +
+                Pattern.quote(name) + ";";
+        this.toType().fileDoesNotContainPattern(pattern);
+        return this;
+    }
+
+    /**
+     * assert that the annotation is imported.
+     *
+     * @param name clasname of the annotation.  For example "Nullable" or a full qualified class name like "java.util.List"
+     */
+    public TypeAnnotationsAssert doesImportAnnotation(final String name) {
+        String pattern = "import\\s+" +
+                (name.contains(".")?"" : "[\\w.]+\\.") +
+                Pattern.quote(name) + ";";
+        this.toType().fileContainsPattern(pattern);
+        return this;
+    }
 }
diff --git a/modules/openapi-generator/src/test/java/org/openapitools/codegen/java/spring/SpringCodegenTest.java b/modules/openapi-generator/src/test/java/org/openapitools/codegen/java/spring/SpringCodegenTest.java
index 58feb32a3b25..573a24198dd6 100644
--- a/modules/openapi-generator/src/test/java/org/openapitools/codegen/java/spring/SpringCodegenTest.java
+++ b/modules/openapi-generator/src/test/java/org/openapitools/codegen/java/spring/SpringCodegenTest.java
@@ -6629,6 +6629,7 @@ public void testJspecify(String library, int springBootVersion, String fooApiFil
                         CONTAINER_DEFAULT_TO_NULL, true,
                         OPENAPI_NULLABLE, false,
                         USE_BEANVALIDATION, true,
+                        INTERFACE_ONLY, false,
                         springVersionProperty, springBootVersion > 2
                 ),
                 codegenConfigurator ->
@@ -6648,12 +6649,14 @@ public void testJspecify(String library, int springBootVersion, String fooApiFil
                     .doesNotContain("findbugs");
         }
         JavaFileAssert.assertThat(files.get("Foo.java"))
+                .assertTypeAnnotations().doesImportAnnotation("org.jspecify.annotations.Nullable").toType()
                 .fileContains(
                         "private java.time.@Nullable Instant dt;",
                         "private org.springframework.core.io.@Nullable Resource binary",
                         "setBinary(org.springframework.core.io.@Nullable Resource binary)"
                 );
         JavaFileAssert.assertThat(files.get(fooApiFilename))
+                .assertTypeAnnotations().doesImportAnnotation("org.jspecify.annotations.Nullable").toType()
                 .fileContains(
                         "java.time.@Nullable Instant dtParam",
                         "java.time.@Nullable Instant dtQuery",
@@ -6663,6 +6666,14 @@ public void testJspecify(String library, int springBootVersion, String fooApiFil
                 .fileContains("@org.jspecify.annotations.NullMarked");
         JavaFileAssert.assertThat(files.get("model/package-info.java"))
                 .fileContains("@org.jspecify.annotations.NullMarked");
+
+        if (SPRING_BOOT.equals(library)) {
+            // Nullable annotation is not (yet) put on NativeWebRequest, but still present as import when useJspecify=true
+            JavaFileAssert.assertThat(files.get("UploadApiController.java").toPath())
+                    .assertTypeAnnotations()
+                    .doesNotContainWithName("Nullable")
+                    .doesImportAnnotation("org.jspecify.annotations.Nullable");
+        }
     }
 
     // -------------------------------------------------------------------------