diff --git a/src/test/suite/vttRoundtrip.integration.test.ts b/src/test/suite/vttRoundtrip.integration.test.ts
index 6208c113a..95056a349 100644
--- a/src/test/suite/vttRoundtrip.integration.test.ts
+++ b/src/test/suite/vttRoundtrip.integration.test.ts
@@ -105,7 +105,7 @@ suite("VTT round-trip integration (mock VTT fixtures)", function () {
         });
         assert.ok(alignedTextCell, "Expected at least one aligned text cell");
 
-        const alignedStart = alignedTextCell!.notebookCell.metadata.data.startTime as number;
+        const alignedStart = alignedTextCell!.notebookCell!.metadata!.data!.startTime as number;
         const expectedContent = importedByStart.get(alignedStart);
         assert.ok(expectedContent, "Expected imported content for aligned text cell");
         assert.strictEqual(
diff --git a/webviews/codex-webviews/src/NewSourceUploader/importers/subtitles/SubtitlesImporterForm.tsx b/webviews/codex-webviews/src/NewSourceUploader/importers/subtitles/SubtitlesImporterForm.tsx
index 083e846cc..70ceee2ee 100644
--- a/webviews/codex-webviews/src/NewSourceUploader/importers/subtitles/SubtitlesImporterForm.tsx
+++ b/webviews/codex-webviews/src/NewSourceUploader/importers/subtitles/SubtitlesImporterForm.tsx
@@ -24,7 +24,7 @@ import {
     AlertCircle,
 } from "lucide-react";
 import { Badge } from "../../../components/ui/badge";
-import { subtitlesImporter } from "./index";
+import { subtitlesImporter, validateSubtitleTimestamps } from "./index";
 import { subtitlesImporterPlugin } from "./index.tsx";
 import { handleImportCompletion, notebookToImportedContent } from "../common/translationHelper";
 import { notifyImportStarted, notifyImportEnded } from "../../utils/importProgress";
@@ -45,6 +45,7 @@ export const SubtitlesImporterForm: React.FC<ImporterComponentProps> = (props) =
     const [result, setResult] = useState<NotebookPair | null>(null);
     const [alignedCells, setAlignedCells] = useState<AlignedCell[] | null>(null);
     const [previewContent, setPreviewContent] = useState<string>("");
+    const [fileWarnings, setFileWarnings] = useState<string[]>([]);
     const [subtitleStats, setSubtitleStats] = useState<{
         totalCues: number;
         duration: string;
@@ -64,6 +65,7 @@ export const SubtitlesImporterForm: React.FC<ImporterComponentProps> = (props) =
             setResult(null);
             setAlignedCells(null);
             setSubtitleStats(null);
+            setFileWarnings([]);
 
             // Show preview and analyze file
             try {
@@ -103,6 +105,9 @@ export const SubtitlesImporterForm: React.FC<ImporterComponentProps> = (props) =
                     duration,
                     format,
                 });
+
+                const timestampWarnings = validateSubtitleTimestamps(text);
+                setFileWarnings(timestampWarnings);
             } catch (err) {
                 console.warn("Could not preview file:", err);
             }
@@ -581,6 +586,17 @@ export const SubtitlesImporterForm: React.FC<ImporterComponentProps> = (props) =
                                 </Card>
                             )}
 
+                            {fileWarnings.length > 0 && (
+                                <Alert className="border-yellow-500 bg-yellow-50 dark:bg-yellow-950">
+                                    <AlertCircle className="h-4 w-4 !text-yellow-600 dark:!text-yellow-400" />
+                                    <AlertDescription className="text-yellow-800 dark:text-yellow-200">
+                                        {fileWarnings.map((warning, index) => (
+                                            <p key={index}>{warning}</p>
+                                        ))}
+                                    </AlertDescription>
+                                </Alert>
+                            )}
+
                             {previewContent && (
                                 <Card>
                                     <CardHeader>
diff --git a/webviews/codex-webviews/src/NewSourceUploader/importers/subtitles/index.test.ts b/webviews/codex-webviews/src/NewSourceUploader/importers/subtitles/index.test.ts
index f14be1fbc..5db3762e9 100644
--- a/webviews/codex-webviews/src/NewSourceUploader/importers/subtitles/index.test.ts
+++ b/webviews/codex-webviews/src/NewSourceUploader/importers/subtitles/index.test.ts
@@ -1,5 +1,5 @@
 import { describe, it, expect } from 'vitest';
-import { subtitlesImporter } from './index';
+import { subtitlesImporter, validateSubtitleTimestamps } from './index';
 
 // Minimal File-like shim for tests
 class MockFile {
@@ -41,4 +41,138 @@ describe('subtitlesImporter.parseFile', () => {
     });
 });
 
+describe('validateSubtitleTimestamps', () => {
+    it('returns no warnings for a well-ordered VTT', () => {
+        const vtt = [
+            'WEBVTT',
+            '',
+            '1',
+            '00:00:01.000 --> 00:00:03.000',
+            'First cue',
+            '',
+            '2',
+            '00:00:04.000 --> 00:00:06.000',
+            'Second cue',
+            '',
+            '3',
+            '00:00:07.000 --> 00:00:09.000',
+            'Third cue',
+        ].join('\n');
 
+        expect(validateSubtitleTimestamps(vtt)).toEqual([]);
+    });
+
+    it('returns no warnings for a well-ordered SRT', () => {
+        const srt = [
+            '1',
+            '00:00:01,000 --> 00:00:03,000',
+            'First cue',
+            '',
+            '2',
+            '00:00:04,000 --> 00:00:06,000',
+            'Second cue',
+        ].join('\n');
+
+        expect(validateSubtitleTimestamps(srt)).toEqual([]);
+    });
+
+    it('catches small overlaps from multi-speaker cues (<5s)', () => {
+        const vtt = [
+            'WEBVTT',
+            '',
+            '1',
+            '00:00:10.000 --> 00:00:14.000',
+            'Speaker A',
+            '',
+            '1',
+            '00:00:10.000 --> 00:00:14.000',
+            'Speaker B (same timestamp, overlap of 4s)',
+        ].join('\n');
+
+        const warnings = validateSubtitleTimestamps(vtt);
+        expect(warnings.length).toBe(1);
+        expect(warnings[0]).toMatch(/non-sequential timestamps/);
+        expect(warnings[0]).toMatch(/4 seconds/);
+    });
+
+    it('warns when timestamps jump backwards significantly (corrupted hour)', () => {
+        const vtt = [
+            'WEBVTT',
+            '',
+            '1',
+            '01:00:23.625 --> 01:00:28.458',
+            'Cue with wrong hour',
+            '',
+            '2',
+            '00:00:52.886 --> 00:00:54.763',
+            'Cue with correct hour (jumps back ~3573s)',
+        ].join('\n');
+
+        const warnings = validateSubtitleTimestamps(vtt);
+        expect(warnings.length).toBe(1);
+        expect(warnings[0]).toMatch(/non-sequential timestamps/);
+        expect(warnings[0]).toMatch(/1 hour/);
+    });
+
+    it('counts multiple out-of-order cues', () => {
+        const vtt = [
+            'WEBVTT',
+            '',
+            '1',
+            '01:00:23.000 --> 01:00:28.000',
+            'Wrong hour',
+            '',
+            '2',
+            '00:00:30.000 --> 00:00:35.000',
+            'Correct (jump back)',
+            '',
+            '3',
+            '01:00:40.000 --> 01:00:45.000',
+            'Wrong hour again',
+            '',
+            '4',
+            '00:00:50.000 --> 00:00:55.000',
+            'Correct (jump back again)',
+        ].join('\n');
+
+        const warnings = validateSubtitleTimestamps(vtt);
+        expect(warnings.length).toBe(1);
+        expect(warnings[0]).toMatch(/2 subtitle cue/);
+    });
+
+    it('reports minutes for moderate jumps', () => {
+        const vtt = [
+            'WEBVTT',
+            '',
+            '1',
+            '00:05:00.000 --> 00:05:30.000',
+            'Later cue first',
+            '',
+            '2',
+            '00:01:00.000 --> 00:01:05.000',
+            'Earlier cue second (jumps back ~270s)',
+        ].join('\n');
+
+        const warnings = validateSubtitleTimestamps(vtt);
+        expect(warnings.length).toBe(1);
+        expect(warnings[0]).toMatch(/\d+ minutes/);
+    });
+
+    it('reports seconds for small jumps', () => {
+        const vtt = [
+            'WEBVTT',
+            '',
+            '1',
+            '00:00:30.000 --> 00:00:40.000',
+            'Later cue first',
+            '',
+            '2',
+            '00:00:10.000 --> 00:00:15.000',
+            'Earlier cue second (jumps back ~30s)',
+        ].join('\n');
+
+        const warnings = validateSubtitleTimestamps(vtt);
+        expect(warnings.length).toBe(1);
+        expect(warnings[0]).toMatch(/\d+ seconds/);
+    });
+});
diff --git a/webviews/codex-webviews/src/NewSourceUploader/importers/subtitles/index.ts b/webviews/codex-webviews/src/NewSourceUploader/importers/subtitles/index.ts
index de280e1fe..be8bbff92 100644
--- a/webviews/codex-webviews/src/NewSourceUploader/importers/subtitles/index.ts
+++ b/webviews/codex-webviews/src/NewSourceUploader/importers/subtitles/index.ts
@@ -20,6 +20,63 @@ import { createSubtitleCellMetadata } from './cellMetadata';
 
 const SUPPORTED_EXTENSIONS = ['vtt', 'srt', 'ass', 'sub'];
 
+/**
+ * Scans raw subtitle text for non-sequential timestamps.
+ * Returns an array of warning strings (empty if no issues found).
+ * Works with both VTT (`.` separator) and SRT (`,` separator) formats.
+ */
+export const validateSubtitleTimestamps = (content: string): string[] => {
+    const warnings: string[] = [];
+    const timestampRegex =
+        /(\d{2}):(\d{2}):(\d{2})[.,](\d{3})\s*-->\s*(\d{2}):(\d{2}):(\d{2})[.,](\d{3})/g;
+
+    let match: RegExpExecArray | null;
+    let prevEndTime = -1;
+    let cueIndex = 0;
+    const majorJumps: { cueIndex: number; jumpBackSeconds: number; }[] = [];
+
+    while ((match = timestampRegex.exec(content)) !== null) {
+        cueIndex++;
+        const startTime =
+            parseInt(match[1]) * 3600 +
+            parseInt(match[2]) * 60 +
+            parseInt(match[3]) +
+            parseInt(match[4]) / 1000;
+        const endTime =
+            parseInt(match[5]) * 3600 +
+            parseInt(match[6]) * 60 +
+            parseInt(match[7]) +
+            parseInt(match[8]) / 1000;
+
+        if (prevEndTime >= 0 && startTime < prevEndTime) {
+            const jumpBack = prevEndTime - startTime;
+            if (jumpBack > 0) {
+                majorJumps.push({ cueIndex, jumpBackSeconds: jumpBack });
+            }
+        }
+        prevEndTime = endTime;
+    }
+
+    if (majorJumps.length > 0) {
+        const maxJump = Math.max(...majorJumps.map((j) => j.jumpBackSeconds));
+        const formattedMaxJump =
+            maxJump >= 3000
+                ? `${Math.round(maxJump / 3600)} hour(s)`
+                : maxJump >= 120
+                    ? `${Math.round(maxJump / 60)} minutes`
+                    : `${Math.round(maxJump)} seconds`;
+
+        warnings.push(
+            `Found ${majorJumps.length} subtitle cue(s) with non-sequential timestamps ` +
+            `(jumping backwards by up to ${formattedMaxJump}). ` +
+            `This typically indicates corrupted timing data (e.g., incorrect hour values). ` +
+            `The imported content may not be in the correct order.`
+        );
+    }
+
+    return warnings;
+};
+
 /**
  * Parses SRT content and converts it to VTT-like structure
  */
@@ -117,6 +174,10 @@ const validateFile = async (file: File): Promise<FileValidationResult> => {
             warnings.push('No timestamp patterns found - this may not be a subtitle file');
         }
 
+        // Check for non-sequential timestamps
+        const timestampWarnings = validateSubtitleTimestamps(content);
+        warnings.push(...timestampWarnings);
+
     } catch (error) {
         errors.push('Could not read file content');
     }
@@ -187,6 +248,8 @@ export const parseFile = async (
             throw new Error('No subtitle cues found in the file');
         }
 
+        const timestampWarnings = validateSubtitleTimestamps(content);
+
         onProgress?.(createProgress('Creating Cells', 'Creating notebook cells...', 70));
 
         // Create notebook cells using ProcessedCell format with cellMetadata
@@ -273,6 +336,7 @@ export const parseFile = async (
         return {
             success: true,
             notebookPair: notebookPairWithMilestones,
+            warnings: timestampWarnings.length > 0 ? timestampWarnings : undefined,
             metadata: {
                 segmentCount: sourceNotebook.cells.length,
                 format,