diff --git a/packages/core/data-transfer/src/engine/diagnostic.ts b/packages/core/data-transfer/src/engine/diagnostic.ts
new file mode 100644
index 0000000000..4ea31ceb2d
--- /dev/null
+++ b/packages/core/data-transfer/src/engine/diagnostic.ts
@@ -0,0 +1,119 @@
+import { EventEmitter } from 'events';
+
+export interface IDiagnosticReporterOptions {
+  stackSize?: number;
+}
+
+export type GenericDiagnostic<K extends DiagnosticKind, T = unknown> = {
+  kind: K;
+  details: {
+    message: string;
+    createdAt: Date;
+  } & T;
+};
+
+export type DiagnosticKind = 'error' | 'warning' | 'info';
+
+export type DiagnosticListener<T extends DiagnosticKind = DiagnosticKind> = (
+  diagnostic: { kind: T } & Diagnostic extends infer U ? U : 'foo'
+) => void | Promise<void>;
+
+export type DiagnosticEvent = 'diagnostic' | `diagnostic.${DiagnosticKind}`;
+
+export type GetEventListener<E extends DiagnosticEvent> = E extends 'diagnostic'
+  ? DiagnosticListener
+  : E extends `diagnostic.${infer K}`
+  ? K extends DiagnosticKind
+    ? DiagnosticListener<K>
+    : never
+  : never;
+
+export type Diagnostic = ErrorDiagnostic | WarningDiagnostic | InfoDiagnostic;
+
+export type ErrorDiagnosticSeverity = 'fatal' | 'error' | 'silly';
+
+export type ErrorDiagnostic = GenericDiagnostic<
+  'error',
+  {
+    name: string;
+    severity: ErrorDiagnosticSeverity;
+    error: Error;
+  }
+>;
+
+export type WarningDiagnostic = GenericDiagnostic<
+  'warning',
+  {
+    origin?: string;
+  }
+>;
+
+export type InfoDiagnostic<T = unknown> = GenericDiagnostic<
+  'info',
+  {
+    params?: T;
+  }
+>;
+
+export interface IDiagnosticReporter {
+  stack: {
+    readonly size: number;
+    readonly items: Diagnostic[];
+  };
+
+  report(diagnostic: Diagnostic): IDiagnosticReporter;
+  onDiagnostic(listener: DiagnosticListener): IDiagnosticReporter;
+  on<T extends DiagnosticKind>(kind: T, listener: DiagnosticListener<T>): IDiagnosticReporter;
+}
+
+const createDiagnosticReporter = (
+  options: IDiagnosticReporterOptions = {}
+): IDiagnosticReporter => {
+  const { stackSize = -1 } = options;
+
+  const emitter = new EventEmitter();
+  const stack: Diagnostic[] = [];
+
+  const addListener = <T extends DiagnosticEvent>(event: T, listener: GetEventListener<T>) => {
+    emitter.on(event, listener);
+  };
+
+  return {
+    stack: {
+      get size() {
+        return stack.length;
+      },
+
+      get items() {
+        return stack;
+      },
+    },
+
+    report(diagnostic: Diagnostic) {
+      emitter.emit('diagnostic', diagnostic);
+      emitter.emit(`diagnostic.${diagnostic.kind}`, diagnostic);
+
+      if (stackSize !== -1 && stack.length >= stackSize) {
+        stack.shift();
+      }
+
+      stack.push(diagnostic);
+
+      return this;
+    },
+
+    onDiagnostic(listener: DiagnosticListener) {
+      addListener('diagnostic', listener);
+
+      return this;
+    },
+
+    on<T extends DiagnosticKind>(kind: T, listener: DiagnosticListener<T>) {
+      addListener(`diagnostic.${kind}`, listener as never);
+
+      return this;
+    },
+  };
+};
+
+export { createDiagnosticReporter };
diff --git a/packages/core/data-transfer/src/engine/errors.ts b/packages/core/data-transfer/src/engine/errors.ts
new file mode 100644
index 0000000000..aedd1bfd47
--- /dev/null
+++ b/packages/core/data-transfer/src/engine/errors.ts
@@ -0,0 +1,33 @@
+import { DataTransferError, Severity, SeverityKind } from '../errors';
+
+type TransferEngineStep = 'initialization' | 'validation' | 'transfer';
+
+type TransferEngineErrorDetails<P extends TransferEngineStep = TransferEngineStep, U = never> = {
+  step: P;
+} & ([U] extends [never] ? unknown : { details?: U });
+
+class TransferEngineError<
+  P extends TransferEngineStep = TransferEngineStep,
+  U = never,
+  T extends TransferEngineErrorDetails<P, U> = TransferEngineErrorDetails<P, U>
+> extends DataTransferError<T> {
+  constructor(severity: Severity, message?: string, details?: T | null) {
+    super('engine', severity, message, details);
+  }
+}
+
+class TransferEngineInitializationError extends TransferEngineError<'initialization'> {
+  constructor(message?: string) {
+    super(SeverityKind.FATAL, message, { step: 'initialization' });
+  }
+}
+
+class TransferEngineValidationError<
+  T extends { check: string } = { check: string }
+> extends TransferEngineError<'validation', T> {
+  constructor(message?: string, details?: T) {
+    super(SeverityKind.FATAL, message, { step: 'validation', details });
+  }
+}
+
+export { TransferEngineError, TransferEngineInitializationError, TransferEngineValidationError };
diff --git a/packages/core/data-transfer/src/engine/index.ts b/packages/core/data-transfer/src/engine/index.ts
index f26706a4e0..14f15e811d 100644
--- a/packages/core/data-transfer/src/engine/index.ts
+++ b/packages/core/data-transfer/src/engine/index.ts
@@ -1,6 +1,7 @@
 import { PassThrough, Transform, Readable, Writable, Stream } from 'stream';
 import { extname } from 'path';
-import { isEmpty, uniq } from 'lodash/fp';
+import { EOL } from 'os';
+import { isEmpty, uniq, last } from 'lodash/fp';
 import { diff as semverDiff } from 'semver';
 import type { Schema } from '@strapi/strapi';
 
@@ -16,12 +17,20 @@ import type {
   ITransferResults,
   TransferStage,
   TransferTransform,
+  IProvider,
 } from '../../types';
 import type { Diff } from '../utils/json';
 
-import { compareSchemas } from './validation/schemas';
+import { compareSchemas, validateProvider } from './validation';
 import { filter, map } from '../utils/stream';
 
+import { TransferEngineValidationError } from './errors';
+import {
+  createDiagnosticReporter,
+  IDiagnosticReporter,
+  ErrorDiagnosticSeverity,
+} from './diagnostic';
+
 export const TRANSFER_STAGES: ReadonlyArray<TransferStage> = Object.freeze([
   'entities',
   'links',
@@ -53,17 +62,13 @@ class TransferEngine<
     stream: PassThrough;
   };
 
-  constructor(
-    sourceProvider: ISourceProvider,
-    destinationProvider: IDestinationProvider,
-    options: ITransferEngineOptions
-  ) {
-    if (sourceProvider.type !== 'source') {
-      throw new Error("SourceProvider does not have type 'source'");
-    }
-    if (destinationProvider.type !== 'destination') {
-      throw new Error("DestinationProvider does not have type 'destination'");
-    }
+  diagnostics: IDiagnosticReporter;
+
+  constructor(sourceProvider: S, destinationProvider: D, options: ITransferEngineOptions) {
+    this.diagnostics = createDiagnosticReporter();
+
+    validateProvider('source', sourceProvider);
+
     this.sourceProvider = sourceProvider;
     this.destinationProvider = destinationProvider;
     this.options = options;
@@ -71,6 +76,56 @@ class TransferEngine<
     this.progress = { data: {}, stream: new PassThrough({ objectMode: true }) };
   }
 
+  /**
+   * Report a fatal error and throw it
+   */
+  #panic(error: Error) {
+    this.#reportError(error, 'fatal');
+
+    throw error;
+  }
+
+  /**
+   * Report an error diagnostic
+   */
+  #reportError(error: Error, severity: ErrorDiagnosticSeverity) {
+    this.diagnostics.report({
+      kind: 'error',
+      details: {
+        severity,
+        createdAt: new Date(),
+        name: error.name,
+        message: error.message,
+        error,
+      },
+    });
+  }
+
+  /**
+   * Report a warning diagnostic
+   */
+  #reportWarning(message: string, origin?: string) {
+    this.diagnostics.report({
+      kind: 'warning',
+      details: { createdAt: new Date(), message, origin },
+    });
+  }
+
+  /**
+   * Report an info diagnostic
+   */
+  #reportInfo(message: string, params?: unknown) {
+    this.diagnostics.report({
+      kind: 'info',
+      details: { createdAt: new Date(), message, params },
+    });
+  }
+
+  /**
+   * Create and return a transform stream based on the given stage and options.
+   *
+   * Allowed transformations includes 'filter' and 'map'.
+   */
   #createStageTransformStream<T extends TransferStage>(
     key: T,
     options: { includeGlobal?: boolean } = {}
@@ -101,6 +156,11 @@ class TransferEngine<
     return stream;
   }
 
+  /**
+   * Update the Engine's transfer progress data for a given stage.
+   *
+   * Providing aggregate options enable custom computation to get the size (bytes) or the aggregate key associated with the data
+   */
   #updateTransferProgress<T = unknown>(
     stage: TransferStage,
     data: T,
@@ -142,6 +202,11 @@ class TransferEngine<
     }
   }
 
+  /**
+   * Create and return a PassThrough stream.
+   *
+   * Upon writing data into it, it'll update the Engine's transfer progress data and trigger stage update events.
+   */
   #progressTracker(
     stage: TransferStage,
     aggregate?: {
@@ -159,10 +224,16 @@ class TransferEngine<
     });
   }
 
+  /**
+   * Shorthand method used to trigger transfer update events to every listeners
+   */
   #emitTransferUpdate(type: 'init' | 'start' | 'finish' | 'error', payload?: object) {
     this.progress.stream.emit(`transfer::${type}`, payload);
   }
 
+  /**
+   * Shorthand method used to trigger stage update events to every listeners
+   */
   #emitStageUpdate(type: 'start' | 'finish' | 'progress' | 'skip', transferStage: TransferStage) {
     this.progress.stream.emit(`stage::${type}`, {
       data: this.progress.data,
@@ -170,9 +241,25 @@ class TransferEngine<
     });
   }
 
+  /**
+   * Run a version check between two strapi version (source and destination) using the strategy given to the engine during initialization.
+   *
+   * If there is a mismatch, throws a validation error.
+   */
   #assertStrapiVersionIntegrity(sourceVersion?: string, destinationVersion?: string) {
     const strategy = this.options.versionStrategy || DEFAULT_VERSION_STRATEGY;
 
+    const reject = () => {
+      throw new TransferEngineValidationError(
+        `The source and destination provide are targeting incompatible Strapi versions (using the "${strategy}" strategy). The source (${this.sourceProvider.name}) version is ${sourceVersion} and the destination (${this.destinationProvider.name}) version is ${destinationVersion}`,
+        {
+          check: 'strapi.version',
+          strategy,
+          versions: { source: sourceVersion, destination: destinationVersion },
+        }
+      );
+    };
+
     if (
       !sourceVersion ||
       !destinationVersion ||
@@ -185,11 +272,10 @@ class TransferEngine<
     let diff;
     try {
       diff = semverDiff(sourceVersion, destinationVersion);
-    } catch (e: unknown) {
-      throw new Error(
-        `Strapi versions doesn't match (${strategy} check): ${sourceVersion} does not match with ${destinationVersion}`
-      );
+    } catch {
+      reject();
     }
+
     if (!diff) {
       return;
     }
@@ -207,13 +293,17 @@ class TransferEngine<
       return;
     }
 
-    throw new Error(
-      `Strapi versions doesn't match (${strategy} check): ${sourceVersion} does not match with ${destinationVersion}`
-    );
+    reject();
   }
 
+  /**
+   * Run a check between two set of schemas (source and destination) using the strategy given to the engine during initialization.
+   *
+   * If there are differences and/or incompatibilities between source and destination schemas, then throw a validation error.
+   */
   #assertSchemasMatching(sourceSchemas: SchemaMap, destinationSchemas: SchemaMap) {
     const strategy = this.options.schemaStrategy || DEFAULT_SCHEMA_STRATEGY;
+
     if (strategy === 'ignore') {
       return;
     }
@@ -232,14 +322,48 @@ class TransferEngine<
     });
 
     if (!isEmpty(diffs)) {
-      throw new Error(
-        `Import process failed because the project doesn't have a matching data structure 
-        ${JSON.stringify(diffs, null, 2)}
-        `
+      const formattedDiffs = Object.entries(diffs)
+        .map(([uid, ctDiffs]) => {
+          let msg = `- ${uid}:${EOL}`;
+
+          msg += ctDiffs
+            .sort((a, b) => (a.kind > b.kind ? -1 : 1))
+            .map((diff) => {
+              if (diff.kind === 'added') {
+                return `Added "${diff.path}": "${diff.value}" (${diff.type})`;
+              }
+
+              if (diff.kind === 'deleted') {
+                return `Removed "${diff.path}"`;
+              }
+
+              if (diff.kind === 'modified') {
+                return `Modified "${diff.path}". "${diff.values[0]}" (${diff.types[0]}) => "${diff.values[1]}" (${diff.types[1]})`;
+              }
+
+              throw new Error(`Invalid diff found for "${uid}"`);
+            })
+            .map((line) => `  - ${line}`)
+            .join(EOL);
+
+          return msg;
+        })
+        .join(EOL);
+
+      throw new TransferEngineValidationError(
+        `Invalid schema changes detected during integrity checks (using the ${strategy} strategy). Please find a summary of the changes below:\n${formattedDiffs}`,
+        {
+          check: 'schema.changes',
+          strategy,
+          diffs,
+        }
       );
     }
   }
 
+  /**
+   * Build a run a stage transfer based on the given parameters.
+   */
   async #transferStage(options: {
     stage: TransferStage;
     source?: Readable;
@@ -251,7 +375,7 @@ class TransferEngine<
 
     if (!source || !destination) {
       // Wait until source and destination are closed
-      await Promise.allSettled(
+      const results = await Promise.allSettled(
         [source, destination].map((stream) => {
           // if stream is undefined or already closed, resolve immediately
           if (!stream || stream.destroyed) {
@@ -265,6 +389,12 @@ class TransferEngine<
         })
       );
 
+      results.forEach((state) => {
+        if (state.status === 'rejected') {
+          this.#reportWarning(state.reason, `transfer(${stage})`);
+        }
+      });
+
       this.#emitStageUpdate('skip', stage);
 
       return;
@@ -283,7 +413,15 @@ class TransferEngine<
         stream = stream.pipe(tracker);
       }
 
-      stream.pipe(destination).on('error', reject).on('close', resolve);
+      stream
+        .pipe(destination)
+        .on('error', (e) => {
+          // TODO ?
+          // this.#reportError(e, 'error');
+          // destination.destroy(e);
+          reject(e);
+        })
+        .on('close', resolve);
     });
 
     this.#emitStageUpdate('finish', stage);
@@ -302,12 +440,36 @@ class TransferEngine<
     }
   }
 
+  /**
+   * Run the bootstrap method in both source and destination providers
+   */
   async bootstrap(): Promise<void> {
-    await Promise.all([this.sourceProvider.bootstrap?.(), this.destinationProvider.bootstrap?.()]);
+    const results = await Promise.allSettled([
+      this.sourceProvider.bootstrap?.(),
+      this.destinationProvider.bootstrap?.(),
+    ]);
+
+    results.forEach((result) => {
+      if (result.status === 'rejected') {
+        this.#panic(result.reason);
+      }
+    });
   }
 
+  /**
+   * Run the close method in both source and destination providers
+   */
   async close(): Promise<void> {
-    await Promise.all([this.sourceProvider.close?.(), this.destinationProvider.close?.()]);
+    const results = await Promise.allSettled([
+      this.sourceProvider.close?.(),
+      this.destinationProvider.bootstrap?.(),
+    ]);
+
+    results.forEach((result) => {
+      if (result.status === 'rejected') {
+        this.#panic(result.reason);
+      }
+    });
   }
 
   async #resolveProviderResource() {
@@ -323,7 +485,7 @@ class TransferEngine<
     }
   }
 
-  async integrityCheck(): Promise<boolean> {
+  async integrityCheck() {
     try {
       const sourceMetadata = await this.sourceProvider.getMetadata();
       const destinationMetadata = await this.destinationProvider.getMetadata();
@@ -341,10 +503,12 @@ class TransferEngine<
       if (sourceSchemas && destinationSchemas) {
         this.#assertSchemasMatching(sourceSchemas, destinationSchemas);
       }
-
-      return true;
     } catch (error) {
-      return false;
+      if (error instanceof Error) {
+        this.#panic(error);
+      }
+
+      throw error;
     }
   }
 
@@ -356,17 +520,13 @@ class TransferEngine<
       this.#emitTransferUpdate('init');
       await this.bootstrap();
       await this.init();
-      const isValidTransfer = await this.integrityCheck();
-      if (!isValidTransfer) {
-        // TODO: provide the log from the integrity check
-        throw new Error(
-          `Unable to transfer the data between ${this.sourceProvider.name} and ${this.destinationProvider.name}.\nPlease refer to the log above for more information.`
-        );
-      }
+
+      await this.integrityCheck();
 
       this.#emitTransferUpdate('start');
 
       await this.beforeTransfer();
+
       // Run the transfer stages
       await this.transferSchemas();
       await this.transferEntities();
@@ -380,9 +540,20 @@ class TransferEngine<
     } catch (e: unknown) {
       this.#emitTransferUpdate('error', { error: e });
 
+      const lastDiagnostic = last(this.diagnostics.stack.items);
+
+      // Do not report an error diagnostic if the last one reported the same error
+      if (
+        e instanceof Error &&
+        (!lastDiagnostic || lastDiagnostic.kind !== 'error' || lastDiagnostic.details.error !== e)
+      ) {
+        this.#reportError(e, 'fatal');
+      }
+
       // Rollback the destination provider if an exception is thrown during the transfer
       // Note: This will be configurable in the future
       await this.destinationProvider.rollback?.(e as Error);
+
       throw e;
     }
 
@@ -394,8 +565,23 @@ class TransferEngine<
   }
 
   async beforeTransfer(): Promise<void> {
-    await this.sourceProvider.beforeTransfer?.();
-    await this.destinationProvider.beforeTransfer?.();
+    const runWithDiagnostic = async (provider: IProvider) => {
+      try {
+        await provider.beforeTransfer?.();
+      } catch (error) {
+        // Error happening during the before transfer step should be considered fatal errors
+        if (error instanceof Error) {
+          this.#panic(error);
+        } else {
+          this.#panic(
+            new Error(`Unknwon error when executing "beforeTransfer" on the ${origin} provider`)
+          );
+        }
+      }
+    };
+
+    await runWithDiagnostic(this.sourceProvider);
+    await runWithDiagnostic(this.destinationProvider);
   }
 
   async transferSchemas(): Promise<void> {
@@ -443,7 +629,7 @@ class TransferEngine<
     const transform = this.#createStageTransformStream(stage);
     const tracker = this.#progressTracker(stage, {
       size: (value: IAsset) => value.stats.size,
-      key: (value: IAsset) => extname(value.filename),
+      key: (value: IAsset) => extname(value.filename) ?? 'NA',
     });
 
     await this.#transferStage({ stage, source, destination, transform, tracker });
@@ -462,10 +648,7 @@ class TransferEngine<
   }
 }
 
-export const createTransferEngine = <
-  S extends ISourceProvider = ISourceProvider,
-  D extends IDestinationProvider = IDestinationProvider
->(
+export const createTransferEngine = <S extends ISourceProvider, D extends IDestinationProvider>(
   sourceProvider: S,
   destinationProvider: D,
   options: ITransferEngineOptions
diff --git a/packages/core/data-transfer/src/engine/validation/index.ts b/packages/core/data-transfer/src/engine/validation/index.ts
index 197f1788ef..9fc174d463 100644
--- a/packages/core/data-transfer/src/engine/validation/index.ts
+++ b/packages/core/data-transfer/src/engine/validation/index.ts
@@ -1 +1,2 @@
-export * as schemas from './schemas';
+export * from './schemas';
+export * from './provider';
diff --git a/packages/core/data-transfer/src/engine/validation/provider.ts b/packages/core/data-transfer/src/engine/validation/provider.ts
new file mode 100644
index 0000000000..b5d95eeece
--- /dev/null
+++ b/packages/core/data-transfer/src/engine/validation/provider.ts
@@ -0,0 +1,27 @@
+import { capitalize } from 'lodash/fp';
+
+import type { IDestinationProvider, ISourceProvider, ProviderType } from '../../../types';
+import { TransferEngineValidationError } from '../errors';
+
+const reject = (reason: string): never => {
+  throw new TransferEngineValidationError(`Invalid provider supplied. ${reason}`);
+};
+
+const validateProvider = <T extends ProviderType>(
+  type: ProviderType,
+  provider?: ([T] extends ['source'] ? ISourceProvider : IDestinationProvider) | null
+) => {
+  if (!provider) {
+    return reject(
+      `Expected an instance of "${capitalize(type)}Provider", but got "${typeof provider}" instead.`
+    );
+  }
+
+  if (provider.type !== type) {
+    return reject(
+      `Expected the provider to be of type "${type}" but got "${provider.type}" instead.`
+    );
+  }
+};
+
+export { validateProvider };
diff --git a/packages/core/data-transfer/src/errors/base.ts b/packages/core/data-transfer/src/errors/base.ts
new file mode 100644
index 0000000000..1d3987a39f
--- /dev/null
+++ b/packages/core/data-transfer/src/errors/base.ts
@@ -0,0 +1,19 @@
+import { Severity } from './constants';
+
+class DataTransferError<T = unknown> extends Error {
+  origin: string;
+
+  severity: Severity;
+
+  details: T | null;
+
+  constructor(origin: string, severity: Severity, message?: string, details?: T | null) {
+    super(message);
+
+    this.origin = origin;
+    this.severity = severity;
+    this.details = details ?? null;
+  }
+}
+
+export { DataTransferError };
diff --git a/packages/core/data-transfer/src/errors/constants.ts b/packages/core/data-transfer/src/errors/constants.ts
new file mode 100644
index 0000000000..6c3964cc3f
--- /dev/null
+++ b/packages/core/data-transfer/src/errors/constants.ts
@@ -0,0 +1,6 @@
+export const SeverityKind = {
+  FATAL: 1,
+  ERROR: 2,
+  SILLY: 3,
+} as const;
+export type Severity = typeof SeverityKind[keyof typeof SeverityKind];
diff --git a/packages/core/data-transfer/src/errors/index.ts b/packages/core/data-transfer/src/errors/index.ts
new file mode 100644
index 0000000000..41bf5eaffb
--- /dev/null
+++ b/packages/core/data-transfer/src/errors/index.ts
@@ -0,0 +1,2 @@
+export * from './constants';
+export * from './base';
diff --git a/packages/core/data-transfer/types/transfer-engine.d.ts b/packages/core/data-transfer/types/transfer-engine.d.ts
index bbf6d588bc..cec7ae9f00 100644
--- a/packages/core/data-transfer/types/transfer-engine.d.ts
+++ b/packages/core/data-transfer/types/transfer-engine.d.ts
@@ -1,7 +1,10 @@
-import type { IAsset, IEntity, ILink } from './common-entities';
-import type { ITransferResults, TransferTransform } from './utils';
-import type { ISourceProvider, IDestinationProvider } from './providers';
+import { PassThrough } from 'stream';
 import type { Schema } from '@strapi/strapi';
+import type { IAsset, IEntity, ILink } from './common-entities';
+import type { ITransferResults, TransferTransform, TransferProgress } from './utils';
+import type { ISourceProvider, IDestinationProvider } from './providers';
+import type { Severity } from '../src/errors';
+import type { DiagnosticReporter } from '../src/engine/diagnostic';
 
 /**
  * Defines the capabilities and properties of the transfer engine
@@ -22,6 +25,18 @@ export interface ITransferEngine<
    * The options used to customize the behavio of the transfer engine
    */
   options: ITransferEngineOptions;
+  /**
+   * A diagnostic reporter instance used to gather information about
+   * errors, warnings and information emitted by the engine
+   */
+  diagnostics: DiagnosticReporter;
+  /**
+   * Utilities used to retrieve transfer progress data
+   */
+  progress: {
+    data: TransferProgress;
+    stream: PassThrough;
+  };
 
   /**
    * Runs the integrity check which will make sure it's possible
@@ -29,7 +44,7 @@ export interface ITransferEngine<
    *
    * Note: It requires to read the content of the source & destination metadata files
    */
-  integrityCheck(): Promise<boolean>;
+  integrityCheck(): Promise<void | never>;
 
   /**
    * Start streaming selected data from the source to the destination
diff --git a/packages/core/strapi/lib/commands/transfer/export.js b/packages/core/strapi/lib/commands/transfer/export.js
index be5d33eb08..fc5029d0e9 100644
--- a/packages/core/strapi/lib/commands/transfer/export.js
+++ b/packages/core/strapi/lib/commands/transfer/export.js
@@ -74,6 +74,29 @@ module.exports = async (opts) => {
     },
   });
 
+  engine.diagnostics
+    .on('error', ({ details }) => {
+      const { createdAt, severity, name, message } = details;
+
+      logger.error(
+        chalk.red(`[${createdAt.toISOString()}] [error] (${severity}) ${name}: ${message}`)
+      );
+    })
+    .on('info', ({ details }) => {
+      const { createdAt, message, params } = details;
+
+      const msg = typeof message === 'function' ? message(params) : message;
+
+      logger.info(chalk.blue(`[${createdAt.toISOString()}] [info] ${msg}`));
+    })
+    .on('warning', ({ details }) => {
+      const { createdAt, origin, message } = details;
+
+      logger.warn(
+        chalk.yellow(`[${createdAt.toISOString()}] [warning] (${origin ?? 'transfer'}) ${message}`)
+      );
+    });
+
   const progress = engine.progress.stream;
 
   const getTelemetryPayload = (/* payload */) => {
@@ -104,9 +127,9 @@ module.exports = async (opts) => {
 
     logger.log(`${chalk.bold('Export process has been completed successfully!')}`);
     logger.log(`Export archive is in ${chalk.green(outFile)}`);
-  } catch (e) {
+  } catch {
     await strapi.telemetry.send('didDEITSProcessFail', getTelemetryPayload());
-    logger.error('Export process failed unexpectedly:', e.toString());
+    logger.error('Export process failed');
     process.exit(1);
   }
 
diff --git a/packages/core/strapi/lib/commands/transfer/import.js b/packages/core/strapi/lib/commands/transfer/import.js
index 72fd378d79..61e36b228b 100644
--- a/packages/core/strapi/lib/commands/transfer/import.js
+++ b/packages/core/strapi/lib/commands/transfer/import.js
@@ -14,6 +14,7 @@ const {
 
 const { isObject } = require('lodash/fp');
 const path = require('path');
+const chalk = require('chalk');
 
 const strapi = require('../../index');
 const { buildTransferTable, DEFAULT_IGNORED_CONTENT_TYPES } = require('./utils');
@@ -83,6 +84,29 @@ module.exports = async (opts) => {
 
   const engine = createTransferEngine(source, destination, engineOptions);
 
+  engine.diagnostics
+    .on('error', ({ details }) => {
+      const { createdAt, severity, name, message } = details;
+
+      logger.error(
+        chalk.red(`[${createdAt.toISOString()}] [error] (${severity}) ${name}: ${message}`)
+      );
+    })
+    .on('info', ({ details }) => {
+      const { createdAt, message, params } = details;
+
+      const msg = typeof message === 'function' ? message(params) : message;
+
+      logger.info(chalk.blue(`[${createdAt.toISOString()}] [info] ${msg}`));
+    })
+    .on('warning', ({ details }) => {
+      const { createdAt, origin, message } = details;
+
+      logger.warn(
+        chalk.yellow(`[${createdAt.toISOString()}] [warning] (${origin ?? 'transfer'}) ${message}`)
+      );
+    });
+
   const progress = engine.progress.stream;
   const getTelemetryPayload = () => {
     return {
@@ -106,8 +130,8 @@ module.exports = async (opts) => {
     logger.info('Import process has been completed successfully!');
   } catch (e) {
     await strapiInstance.telemetry.send('didDEITSProcessFail', getTelemetryPayload());
-    logger.error('Import process failed unexpectedly:');
-    logger.error(e);
+    logger.error('Import process failed');
+
     process.exit(1);
   }