diff --git a/generators/base-core/generator.ts b/generators/base-core/generator.ts
index fe753fc6561f..3114761d0960 100644
--- a/generators/base-core/generator.ts
+++ b/generators/base-core/generator.ts
@@ -172,7 +172,6 @@ export default class CoreGenerator extends YeomanGenerator<JHipsterGeneratorOpti
       ...features,
     });
 
-    let jhipsterOldVersion = null;
     if (!this.options.help) {
       /* Force config to use 'generator-jhipster' namespace. */
       this._config = this._getStorage('generator-jhipster');
@@ -180,8 +179,7 @@ export default class CoreGenerator extends YeomanGenerator<JHipsterGeneratorOpti
       /* JHipster config using proxy mode used as a plain object instead of using get/set. */
       this.jhipsterConfig = this.config.createProxy();
 
-      jhipsterOldVersion = this.jhipsterConfig.jhipsterVersion ?? null;
-      this.sharedData = this.createSharedData({ jhipsterOldVersion, help: this.options.help }) as any;
+      this.sharedData = this.createSharedData({ help: this.options.help }) as any;
 
       /* Options parsing must be executed after forcing jhipster storage namespace and after sharedData have been populated */
       this.parseJHipsterOptions(command.options);
@@ -1255,13 +1253,7 @@ templates: ${JSON.stringify(existingTemplates, null, 2)}`;
     return this.options.sharedData.applications?.[this.calculateApplicationId(applicationFolder)];
   }
 
-  private createSharedData({
-    jhipsterOldVersion,
-    help,
-  }: {
-    jhipsterOldVersion: string | null;
-    help?: boolean;
-  }): SharedData<BaseApplication> {
+  private createSharedData({ help }: { help?: boolean }): SharedData<BaseApplication> {
     const applicationId = this.options.applicationId ?? this.calculateApplicationId(this.destinationPath());
     if (this.options.sharedData.applications === undefined) {
       this.options.sharedData.applications = {};
@@ -1272,6 +1264,10 @@ templates: ${JSON.stringify(existingTemplates, null, 2)}`;
     }
     const { ignoreNeedlesError } = this.options;
 
-    return new SharedData<BaseApplication>(sharedApplications[applicationId], { jhipsterOldVersion, ignoreNeedlesError });
+    return new SharedData<BaseApplication>(
+      sharedApplications[applicationId],
+      { destinationPath: this.destinationPath(), memFs: this.env.sharedFs, log: this.log, logCwd: this.env.logCwd },
+      { ignoreNeedlesError },
+    );
   }
 }
diff --git a/generators/base/shared-data.ts b/generators/base/shared-data.ts
index 1e11725feaf0..aa495a655f9c 100644
--- a/generators/base/shared-data.ts
+++ b/generators/base/shared-data.ts
@@ -16,17 +16,37 @@
  * See the License for the specific language governing permissions and
  * limitations under the License.
  */
+import { existsSync, readFileSync, statSync } from 'fs';
+import { rm } from 'fs/promises';
+import { isAbsolute, join, relative } from 'path';
+import { lt as semverLessThan } from 'semver';
 import { defaults } from 'lodash-es';
+import { MemFsEditor, create } from 'mem-fs-editor';
 import { type BaseApplication } from '../base-application/types.js';
 import { type Control } from './types.js';
+import { GENERATOR_JHIPSTER } from '../generator-constants.js';
 
 export default class SharedData<ApplicationType extends BaseApplication = BaseApplication> {
   _storage: any;
+  _editor: MemFsEditor;
+  _log: any;
+  _logCwd: string;
 
-  constructor(storage, initialControl: Partial<Control> = {}) {
+  constructor(storage, { memFs, destinationPath, log, logCwd }, initialControl: Partial<Control> = {}) {
     if (!storage) {
       throw new Error('Storage is required for SharedData');
     }
+
+    this._editor = create(memFs);
+    this._log = log;
+    this._logCwd = logCwd;
+
+    let jhipsterOldVersion;
+    if (existsSync(join(destinationPath, '.yo-rc.json'))) {
+      jhipsterOldVersion = JSON.parse(readFileSync(join(destinationPath, '.yo-rc.json'), 'utf-8').toString())[GENERATOR_JHIPSTER]
+        ?.jhipsterVersion;
+    }
+
     // Backward compatibility sharedData
     this._storage = storage;
 
@@ -44,6 +64,55 @@ export default class SharedData<ApplicationType extends BaseApplication = BaseAp
       nodeDependencies: {},
       customizeTemplatePaths: [],
     });
+
+    let customizeRemoveFiles: Array<(file: string) => string | undefined> = [];
+    const removeFiles = async (assertions: { removedInVersion?: string } | string, ...files: string[]) => {
+      if (typeof assertions === 'string') {
+        files = [assertions, ...files];
+        assertions = {};
+      }
+
+      for (const customize of customizeRemoveFiles) {
+        files = files.map(customize).filter(file => file) as string[];
+      }
+
+      const { removedInVersion } = assertions;
+      if (removedInVersion && jhipsterOldVersion && !semverLessThan(jhipsterOldVersion, removedInVersion)) {
+        return;
+      }
+
+      const absolutePaths = files.map(file => (isAbsolute(file) ? file : join(destinationPath, file)));
+      // Delete from memory fs to keep updated.
+      this._editor.delete(absolutePaths);
+      await Promise.all(
+        absolutePaths.map(async file => {
+          const relativePath = relative(logCwd, file);
+          try {
+            if (statSync(file).isFile()) {
+              this._log.info(`Removing legacy file ${relativePath}`);
+              await rm(file, { force: true });
+            }
+          } catch {
+            this._log.info(`Could not remove legacy file ${relativePath}`);
+          }
+        }),
+      );
+    };
+
+    defaults(this._storage.control, {
+      jhipsterOldVersion,
+      removeFiles,
+      customizeRemoveFiles: [],
+      cleanupFiles: async (cleanup: Record<string, string[]>) => {
+        await Promise.all(
+          Object.entries(cleanup).map(async ([version, files]) => {
+            await removeFiles({ removedInVersion: version }, ...files);
+          }),
+        );
+      },
+    });
+
+    customizeRemoveFiles = this._storage.control.customizeRemoveFiles;
   }
 
   getSource() {
diff --git a/generators/base/types.d.ts b/generators/base/types.d.ts
index 10b345c124d7..a8bdf235aaf2 100644
--- a/generators/base/types.d.ts
+++ b/generators/base/types.d.ts
@@ -13,4 +13,7 @@ export type Control = {
   reproducibleLiquibaseTimestamp?: Date;
   filterEntitiesForClient?: (entity: Entity[]) => Entity[];
   filterEntitiesAndPropertiesForClient?: (entity: Entity[]) => Entity[];
+  customizeRemoveFiles: Array<(file: string) => string | undefined>;
+  removeFiles: (options: { removedInVersion: string } | string, ...files: string[]) => Promise<void>;
+  cleanupFiles: (cleanup: Record<string, string[]>) => Promise<void>;
 };
diff --git a/generators/generate-blueprint/generator.js b/generators/generate-blueprint/generator.js
index 0e9a6a9b6ecb..58fbd5f460b1 100644
--- a/generators/generate-blueprint/generator.js
+++ b/generators/generate-blueprint/generator.js
@@ -173,7 +173,7 @@ export default class extends BaseGenerator {
   }
 
   get preparing() {
-    return {
+    return this.asPreparingTaskGroup({
       prepareCommands() {
         this.application.commands = [];
         this.application.nodeVersion = NODE_VERSION;
@@ -195,7 +195,7 @@ export default class extends BaseGenerator {
           this.application.cliName = cliName ?? `jhipster-${baseName}`;
         }
       },
-    };
+    });
   }
 
   get [BaseGenerator.PREPARING]() {
@@ -203,7 +203,10 @@ export default class extends BaseGenerator {
   }
 
   get writing() {
-    return {
+    return this.asWritingTaskGroup({
+      async cleanup({ control }) {
+        await control.cleanupFiles({ '8.5.1': ['.eslintrc.json'] });
+      },
       async writing() {
         this.application.sampleWritten = this.jhipsterConfig.sampleWritten;
         await this.writeFiles({
@@ -243,7 +246,7 @@ export default class extends BaseGenerator {
           subGeneratorStorage.set(WRITTEN, true);
         }
       },
-    };
+    });
   }
 
   get [BaseGenerator.WRITING]() {
diff --git a/generators/languages/generator.spec.js b/generators/languages/generator.spec.js
index 1f22a527ecb4..76ccfd8ec7ea 100644
--- a/generators/languages/generator.spec.js
+++ b/generators/languages/generator.spec.js
@@ -49,7 +49,8 @@ describe(`generator - ${generator}`, () => {
             nativeLanguage: 'in',
             languages: ['in'],
             baseName: 'jhipster',
-          }),
+          })
+          .commitFiles(),
       );
       it('should migrate in language to id', () => {
         runResult.assertJsonFileContent('.yo-rc.json', {