diff --git a/packages/cli/src/commands/org/config/monitor.ts b/packages/cli/src/commands/org/config/monitor.ts
index 5da4555453..9b4134fd18 100644
--- a/packages/cli/src/commands/org/config/monitor.ts
+++ b/packages/cli/src/commands/org/config/monitor.ts
@@ -1,7 +1,6 @@
 import {ResourceSnapshotsReportModel} from '@coveord/platform-client';
 import {flags, Command} from '@oclif/command';
 import {cli} from 'cli-ux';
-import dedent from 'ts-dedent';
 import {
   buildAnalyticsFailureHook,
   buildAnalyticsSuccessHook,
@@ -17,10 +16,10 @@ import {
   waitFlag,
   getTargetOrg,
   handleSnapshotError,
+  handleReportWithErrors,
 } from '../../../lib/snapshot/snapshotCommon';
 import {SnapshotFactory} from '../../../lib/snapshot/snapshotFactory';
 import {SnapshotReporter} from '../../../lib/snapshot/snapshotReporter';
-import {SnapshotUrlBuilder} from '../../../lib/snapshot/snapshotUrlBuilder';
 
 export default class Monitor extends Command {
   public static description = 'Monitor a Snapshot operation';
@@ -77,29 +76,12 @@ export default class Monitor extends Command {
     reporter: SnapshotReporter
   ) {
     if (!reporter.isSuccessReport()) {
-      await this.displaySnapshotError(snapshot, reporter);
+      const cfg = await this.configuration.get();
+      cli.log(ReportViewerStyles.error(reporter.resultCode));
+      await handleReportWithErrors(snapshot, cfg);
     }
   }
 
-  // TODO: CDX-533: use Custom error instead
-  private async displaySnapshotError(
-    snapshot: Snapshot,
-    reporter: SnapshotReporter
-  ) {
-    cli.log(ReportViewerStyles.error(reporter.resultCode));
-    cli.log();
-    const cfg = await this.configuration.get();
-    const urlBuilder = new SnapshotUrlBuilder(cfg);
-    const snapshotUrl = urlBuilder.getSnapshotPage(snapshot);
-
-    cli.error(
-      dedent`Invalid snapshot - ${snapshot.latestReport.resultCode}.
-
-        You can also use this link to view the snapshot in the Coveo Admin Console:
-        ${snapshotUrl}`
-    );
-  }
-
   private printHeader() {
     const {args} = this.parse(Monitor);
     const snapshotId = args.snapshotId;
diff --git a/packages/cli/src/lib/errors/snapshotErrors.ts b/packages/cli/src/lib/errors/snapshotErrors.ts
index a8fd312336..cfaf160f1f 100644
--- a/packages/cli/src/lib/errors/snapshotErrors.ts
+++ b/packages/cli/src/lib/errors/snapshotErrors.ts
@@ -1,12 +1,48 @@
 import {blueBright} from 'chalk';
+import {cli} from 'cli-ux';
 import dedent from 'ts-dedent';
 import {Configuration} from '../config/config';
 import {Snapshot} from '../snapshot/snapshot';
 import {SnapshotUrlBuilder} from '../snapshot/snapshotUrlBuilder';
 
-export class SnapshotOperationTimeoutError extends Error {
-  public constructor(public snapshot: Snapshot) {
+enum SeverityLevel {
+  Info = 'info',
+  Warn = 'warn',
+  Error = 'error',
+}
+
+interface IDetailedReportable extends SnapshotError {
+  snapshot: Snapshot;
+  level: SeverityLevel;
+  projectPath?: string;
+}
+
+function trySavingDetailedReport(error: IDetailedReportable) {
+  if (error.projectPath) {
+    const reportPath = error.snapshot.saveDetailedReport(error.projectPath);
+    error.message += dedent`\n\n
+          Detailed report saved at ${reportPath}`;
+  }
+}
+
+export class SnapshotError extends Error {
+  public constructor(public level: SeverityLevel) {
     super();
+  }
+
+  public print() {
+    cli.log();
+    cli[this.level]('\n' + this.message);
+  }
+}
+
+export class SnapshotOperationTimeoutError
+  extends SnapshotError
+  implements IDetailedReportable
+{
+  public name = 'Snapshot Operation Timeout Error';
+  public constructor(public snapshot: Snapshot) {
+    super(SeverityLevel.Info);
     this.message = dedent`${
       snapshot.latestReport.type
     } operation is taking a long time to complete.
@@ -16,9 +52,17 @@ export class SnapshotOperationTimeoutError extends Error {
   }
 }
 
-export class SnapshotSynchronizationError extends Error {
-  public constructor(public snapshot: Snapshot, public cfg: Configuration) {
-    super();
+export class SnapshotSynchronizationError
+  extends SnapshotError
+  implements IDetailedReportable
+{
+  public name = 'Snapshot Synchronization Error';
+  public constructor(
+    public snapshot: Snapshot,
+    public cfg: Configuration,
+    public projectPath?: string
+  ) {
+    super(SeverityLevel.Warn);
     const urlBuilder = new SnapshotUrlBuilder(cfg);
     const synchronizationPlanUrl = urlBuilder.getSynchronizationPage(snapshot);
 
@@ -26,24 +70,30 @@ export class SnapshotSynchronizationError extends Error {
       Some conflicts were detected while comparing changes between the snapshot and the target organization.
       Click on the URL below to synchronize your snapshot with your organization before running another push command.
       ${synchronizationPlanUrl}`;
+
+    trySavingDetailedReport(this);
   }
 }
 
-export class SnapshotGenericError extends Error {
+export class SnapshotGenericError
+  extends SnapshotError
+  implements IDetailedReportable
+{
+  public name = 'Snapshot Error';
   public constructor(
     public snapshot: Snapshot,
     public cfg: Configuration,
-    public pathToReport: string
+    public projectPath?: string
   ) {
-    super();
+    super(SeverityLevel.Error);
     const report = snapshot.latestReport;
     const urlBuilder = new SnapshotUrlBuilder(cfg);
     const snapshotUrl = urlBuilder.getSnapshotPage(snapshot);
 
     this.message = dedent`Invalid snapshot - ${report.resultCode}.
-      Detailed report saved at ${pathToReport}.
-
       You can also use this link to view the snapshot in the Coveo Admin Console
       ${snapshotUrl}`;
+
+    trySavingDetailedReport(this);
   }
 }
diff --git a/packages/cli/src/lib/snapshot/snapshotCommon.ts b/packages/cli/src/lib/snapshot/snapshotCommon.ts
index f1725de7f6..5afc86b199 100644
--- a/packages/cli/src/lib/snapshot/snapshotCommon.ts
+++ b/packages/cli/src/lib/snapshot/snapshotCommon.ts
@@ -5,8 +5,8 @@ import {Snapshot, WaitUntilDoneOptions} from './snapshot';
 import {red, green} from 'chalk';
 import {normalize} from 'path';
 import {Config, Configuration} from '../config/config';
-import {SnapshotOperationTimeoutError} from '../errors';
 import {
+  SnapshotError,
   SnapshotGenericError,
   SnapshotSynchronizationError,
 } from '../errors/snapshotErrors';
@@ -69,24 +69,22 @@ export function cleanupProject(projectPath: string) {
 export async function handleReportWithErrors(
   snapshot: Snapshot,
   cfg: Configuration,
-  projectPath: string
+  projectPath?: string
 ) {
   if (snapshot.requiresSynchronization()) {
-    throw new SnapshotSynchronizationError(snapshot, cfg);
+    throw new SnapshotSynchronizationError(snapshot, cfg, projectPath);
   }
 
-  const pathToReport = snapshot.saveDetailedReport(projectPath);
-  throw new SnapshotGenericError(snapshot, cfg, pathToReport);
+  throw new SnapshotGenericError(snapshot, cfg, projectPath);
 }
 
 export function handleSnapshotError(err?: Error) {
-  if (err instanceof SnapshotOperationTimeoutError) {
-    cli.action.stop('Incomplete');
-    cli.log(err.message);
-  } else if (err instanceof SnapshotSynchronizationError) {
-    cli.warn(err.message);
-  } else if (err instanceof SnapshotGenericError) {
-    cli.error(err.message);
+  if (cli.action.running) {
+    cli.action.stop(err?.name);
+  }
+
+  if (err instanceof SnapshotError) {
+    err.print();
   } else {
     throw err;
   }