diff --git a/src/main/java/com/williamcallahan/javachat/service/ingestion/LocalDocsFileIngestionProcessor.java b/src/main/java/com/williamcallahan/javachat/service/ingestion/LocalDocsFileIngestionProcessor.java
index 7c28bbcc..8e5adad9 100644
--- a/src/main/java/com/williamcallahan/javachat/service/ingestion/LocalDocsFileIngestionProcessor.java
+++ b/src/main/java/com/williamcallahan/javachat/service/ingestion/LocalDocsFileIngestionProcessor.java
@@ -297,7 +297,10 @@ private FilePreparation prepare(Path root, Path file, Map<Path, String> ingestio
                 GuardDecision guardDecision = contentGuard.evaluate(new GuardInput(bodyText, parsedDocument));
                 if (!guardDecision.acceptable()) {
                     String rejectionReason = guardDecision.rejectionReason();
-                    return deferred(() -> quarantineRejectedFile(file, rejectionReason));
+                    final boolean replacementRequired = requiresFullReindex;
+                    final MarkerContext rejectedMarkerContext = markerContext;
+                    return deferred(
+                            () -> quarantineRejectedFile(rejectedMarkerContext, replacementRequired, rejectionReason));
                 }
             }
         }
@@ -731,22 +734,55 @@ private static boolean isNavigationOnlyDocument(org.jsoup.nodes.Document parsedD
         return navigationFrameset || interactiveApiReferenceShell;
     }
 
-    private LocalDocsFileOutcome quarantineRejectedFile(Path file, String rejectionReason) {
+    private LocalDocsFileOutcome quarantineRejectedFile(
+            MarkerContext markerContext, boolean requiresFullReindex, String rejectionReason) {
+        Path file = markerContext.file();
+        String contentGuardPhase;
+        String contentGuardDetails;
         try {
             var quarantineService = fileContentServices.quarantine();
             IngestionQuarantineService.QuarantineResult quarantineCopy = quarantineService.quarantine(file);
             INDEXING_LOG.warn("[INDEXING] Content guard rejected file and copied it to quarantine");
-            return LocalDocsFileOutcome.failedFile(new IngestionLocalFailure(
-                    file.toString(),
-                    "content-guard",
-                    "quarantine copy " + quarantineCopy.quarantined() + ": " + rejectionReason));
+            contentGuardPhase = "content-guard";
+            contentGuardDetails = "quarantine copy " + quarantineCopy.quarantined() + ": " + rejectionReason;
         } catch (IOException quarantineException) {
             log.warn(
                     "Failed to quarantine invalid content (exception type: {})",
                     quarantineException.getClass().getSimpleName());
-            return LocalDocsFileOutcome.failedFile(
-                    failureFactory.failure(file, "quarantine-write", quarantineException));
+            contentGuardPhase = "quarantine-write";
+            contentGuardDetails = failureFactory
+                    .failure(file, "quarantine-write", quarantineException)
+                    .details();
+        }
+        if (requiresFullReindex) {
+            try {
+                storage.hybridVector().deleteByUrl(markerContext.collectionKind(), markerContext.url());
+                ingestedFilePruneService.pruneObsoleteLocalStateAfterReplacement(
+                        markerContext.url(),
+                        markerContext.priorIngestionRecord().orElse(null),
+                        List.of());
+            } catch (IOException pruneException) {
+                return LocalDocsFileOutcome.failedFile(failureFactory.failure(file, "prune-local", pruneException));
+            } catch (RuntimeException pruneException) {
+                return LocalDocsFileOutcome.failedFile(failureFactory.failure(file, "prune-runtime", pruneException));
+            }
+            try {
+                markFileIngested(
+                        markerContext.url(),
+                        new FileIngestionRecord(
+                                markerContext.fileSizeBytes(),
+                                markerContext.lastModifiedMillis(),
+                                markerContext.ingestionFingerprint(),
+                                LOCAL_DOCS_EXTRACTION_SEMANTICS_VERSION,
+                                markerContext.collectionName(),
+                                List.of()));
+            } catch (RuntimeException markerTransitionException) {
+                return LocalDocsFileOutcome.failedFile(
+                        failureFactory.failure(file, "marker-transition", markerTransitionException));
+            }
         }
+        return LocalDocsFileOutcome.failedFile(
+                new IngestionLocalFailure(file.toString(), contentGuardPhase, contentGuardDetails));
     }
 
     private LocalDocsFileOutcome markPreviouslyIngestedFile(
diff --git a/src/test/java/com/williamcallahan/javachat/service/ingestion/LocalDocsFileIngestionProcessorTest.java b/src/test/java/com/williamcallahan/javachat/service/ingestion/LocalDocsFileIngestionProcessorTest.java
index fff31daf..2dd406e4 100644
--- a/src/test/java/com/williamcallahan/javachat/service/ingestion/LocalDocsFileIngestionProcessorTest.java
+++ b/src/test/java/com/williamcallahan/javachat/service/ingestion/LocalDocsFileIngestionProcessorTest.java
@@ -468,6 +468,177 @@ void shouldStopBeforeLaterFileWhenContentIsRejected(@TempDir Path temporaryDirec
                 .processAndStoreChunks(anyString(), anyString(), anyString(), anyString());
     }
 
+    @Test
+    void shouldNotLeaveStaleVectorsWhenPreviouslyIngestedFileIsGuardRejected(@TempDir Path temporaryDirectory)
+            throws IOException {
+        DocumentationSource documentationSource =
+                DocsSourceRegistry.documentationSources().getFirst();
+        Path selectedDocumentationRoot =
+                temporaryDirectory.resolve("corpus").resolve(documentationSource.relativeMirrorPath());
+        Files.createDirectories(selectedDocumentationRoot);
+        Path rejectedFile = selectedDocumentationRoot.resolve("rejected.html");
+        Files.writeString(
+                rejectedFile,
+                "<html><head><title>404 Not Found</title></head><body><h1>404 Not Found</h1></body></html>",
+                StandardCharsets.UTF_8);
+        String expectedUrl = DocsSourceRegistry.resolveMirroredPath(selectedDocumentationRoot, rejectedFile)
+                .orElseThrow();
+        FileIngestionRecord priorIngestionRecord = new FileIngestionRecord(
+                Files.size(rejectedFile),
+                Files.getLastModifiedTime(rejectedFile).toMillis(),
+                "prior-good-fingerprint",
+                LocalDocsFileIngestionProcessor.LOCAL_DOCS_EXTRACTION_SEMANTICS_VERSION,
+                "documentation",
+                List.of("prior-chunk-hash"));
+
+        LocalDocsIngestionFixture ingestionFixture = new LocalDocsIngestionFixture();
+        when(ingestionFixture.fileIngestionMarkerStore.readFileIngestionRecord(expectedUrl))
+                .thenReturn(Optional.of(priorIngestionRecord));
+        when(ingestionFixture.hybridVectorService.resolveCollectionName(any())).thenReturn("documentation");
+        when(ingestionFixture.quarantineService.quarantine(rejectedFile))
+                .thenReturn(new IngestionQuarantineService.QuarantineResult(
+                        rejectedFile, temporaryDirectory.resolve("quarantine/rejected.html")));
+
+        LocalDocsFileOutcome outcome =
+                ingestionFixture.ingestionProcessor().process(selectedDocumentationRoot, rejectedFile);
+
+        assertFalse(outcome.processed());
+        assertEquals("content-guard", outcome.failure().orElseThrow().phase());
+        verify(ingestionFixture.quarantineService).quarantine(rejectedFile);
+        verify(ingestionFixture.hybridVectorService).deleteByUrl(any(QdrantCollectionKind.class), eq(expectedUrl));
+        verify(ingestionFixture.ingestedFilePruneService)
+                .pruneObsoleteLocalStateAfterReplacement(expectedUrl, priorIngestionRecord, List.of());
+        ArgumentCaptor<FileIngestionRecord> markerCaptor = ArgumentCaptor.forClass(FileIngestionRecord.class);
+        verify(ingestionFixture.fileIngestionMarkerStore).markFileIngested(eq(expectedUrl), markerCaptor.capture());
+        FileIngestionRecord rejectedIngestionRecord = markerCaptor.getValue();
+        assertTrue(rejectedIngestionRecord.chunkHashes().isEmpty());
+        verify(ingestionFixture.chunkProcessingService, never())
+                .processAndStoreChunks(anyString(), anyString(), anyString(), anyString());
+    }
+
+    @Test
+    void shouldNotLeaveStaleVectorsWhenQuarantineWriteFailsForPreviouslyIngestedFile(@TempDir Path temporaryDirectory)
+            throws IOException {
+        DocumentationSource documentationSource =
+                DocsSourceRegistry.documentationSources().getFirst();
+        Path selectedDocumentationRoot =
+                temporaryDirectory.resolve("corpus").resolve(documentationSource.relativeMirrorPath());
+        Files.createDirectories(selectedDocumentationRoot);
+        Path rejectedFile = selectedDocumentationRoot.resolve("rejected.html");
+        Files.writeString(
+                rejectedFile,
+                "<html><head><title>404 Not Found</title></head><body><h1>404 Not Found</h1></body></html>",
+                StandardCharsets.UTF_8);
+        String expectedUrl = DocsSourceRegistry.resolveMirroredPath(selectedDocumentationRoot, rejectedFile)
+                .orElseThrow();
+        FileIngestionRecord priorIngestionRecord = new FileIngestionRecord(
+                Files.size(rejectedFile),
+                Files.getLastModifiedTime(rejectedFile).toMillis(),
+                "prior-good-fingerprint",
+                LocalDocsFileIngestionProcessor.LOCAL_DOCS_EXTRACTION_SEMANTICS_VERSION,
+                "documentation",
+                List.of("prior-chunk-hash"));
+
+        LocalDocsIngestionFixture ingestionFixture = new LocalDocsIngestionFixture();
+        when(ingestionFixture.fileIngestionMarkerStore.readFileIngestionRecord(expectedUrl))
+                .thenReturn(Optional.of(priorIngestionRecord));
+        when(ingestionFixture.hybridVectorService.resolveCollectionName(any())).thenReturn("documentation");
+        doThrow(new IOException("quarantine storage unavailable"))
+                .when(ingestionFixture.quarantineService)
+                .quarantine(rejectedFile);
+
+        LocalDocsFileOutcome outcome =
+                ingestionFixture.ingestionProcessor().process(selectedDocumentationRoot, rejectedFile);
+
+        assertFalse(outcome.processed());
+        assertEquals("quarantine-write", outcome.failure().orElseThrow().phase());
+        verify(ingestionFixture.quarantineService).quarantine(rejectedFile);
+        verify(ingestionFixture.hybridVectorService).deleteByUrl(any(QdrantCollectionKind.class), eq(expectedUrl));
+        verify(ingestionFixture.ingestedFilePruneService)
+                .pruneObsoleteLocalStateAfterReplacement(expectedUrl, priorIngestionRecord, List.of());
+        ArgumentCaptor<FileIngestionRecord> markerCaptor = ArgumentCaptor.forClass(FileIngestionRecord.class);
+        verify(ingestionFixture.fileIngestionMarkerStore).markFileIngested(eq(expectedUrl), markerCaptor.capture());
+        FileIngestionRecord rejectedIngestionRecord = markerCaptor.getValue();
+        assertTrue(rejectedIngestionRecord.chunkHashes().isEmpty());
+        verify(ingestionFixture.chunkProcessingService, never())
+                .processAndStoreChunks(anyString(), anyString(), anyString(), anyString());
+    }
+
+    @Test
+    void shouldBeIdempotentOnNextRunAfterGuardRejectedPreviouslyIngestedFile(@TempDir Path temporaryDirectory)
+            throws IOException {
+        DocumentationSource documentationSource =
+                DocsSourceRegistry.documentationSources().getFirst();
+        Path selectedDocumentationRoot =
+                temporaryDirectory.resolve("corpus").resolve(documentationSource.relativeMirrorPath());
+        Files.createDirectories(selectedDocumentationRoot);
+        Path rejectedFile = selectedDocumentationRoot.resolve("rejected.html");
+        Files.writeString(
+                rejectedFile,
+                "<html><head><title>404 Not Found</title></head><body><h1>404 Not Found</h1></body></html>",
+                StandardCharsets.UTF_8);
+        String expectedUrl = DocsSourceRegistry.resolveMirroredPath(selectedDocumentationRoot, rejectedFile)
+                .orElseThrow();
+        FileIngestionRecord priorIngestionRecord = new FileIngestionRecord(
+                Files.size(rejectedFile),
+                Files.getLastModifiedTime(rejectedFile).toMillis(),
+                "prior-good-fingerprint",
+                LocalDocsFileIngestionProcessor.LOCAL_DOCS_EXTRACTION_SEMANTICS_VERSION,
+                "documentation",
+                List.of("prior-chunk-hash"));
+
+        LocalDocsIngestionFixture ingestionFixture = new LocalDocsIngestionFixture();
+        Map<String, FileIngestionRecord> markerStore = new HashMap<>();
+        markerStore.put(expectedUrl, priorIngestionRecord);
+        when(ingestionFixture.fileIngestionMarkerStore.readFileIngestionRecord(anyString()))
+                .thenAnswer(invocation -> Optional.ofNullable(markerStore.get(invocation.getArgument(0))));
+        doAnswer(invocation -> {
+                    markerStore.put(invocation.getArgument(0), invocation.getArgument(1));
+                    return null;
+                })
+                .when(ingestionFixture.fileIngestionMarkerStore)
+                .markFileIngested(anyString(), any(FileIngestionRecord.class));
+        when(ingestionFixture.hybridVectorService.resolveCollectionName(any())).thenReturn("documentation");
+        when(ingestionFixture.quarantineService.quarantine(rejectedFile))
+                .thenReturn(new IngestionQuarantineService.QuarantineResult(
+                        rejectedFile, temporaryDirectory.resolve("quarantine/rejected.html")));
+
+        LocalDocsFileOutcome firstOutcome =
+                ingestionFixture.ingestionProcessor().process(selectedDocumentationRoot, rejectedFile);
+
+        assertFalse(firstOutcome.processed());
+        assertEquals("content-guard", firstOutcome.failure().orElseThrow().phase());
+        verify(ingestionFixture.hybridVectorService).deleteByUrl(any(QdrantCollectionKind.class), eq(expectedUrl));
+        verify(ingestionFixture.ingestedFilePruneService)
+                .pruneObsoleteLocalStateAfterReplacement(expectedUrl, priorIngestionRecord, List.of());
+        verify(ingestionFixture.fileIngestionMarkerStore)
+                .markFileIngested(eq(expectedUrl), any(FileIngestionRecord.class));
+
+        clearInvocations(
+                ingestionFixture.chunkProcessingService,
+                ingestionFixture.hybridVectorService,
+                ingestionFixture.fileIngestionMarkerStore,
+                ingestionFixture.ingestedFilePruneService,
+                ingestionFixture.quarantineService);
+        when(ingestionFixture.hybridVectorService.hasExactPointIdsForUrl(
+                        any(QdrantCollectionKind.class), eq(expectedUrl), eq(List.of())))
+                .thenReturn(true);
+
+        LocalDocsFileOutcome repeatedOutcome =
+                ingestionFixture.ingestionProcessor().process(selectedDocumentationRoot, rejectedFile);
+
+        assertFalse(repeatedOutcome.processed());
+        assertTrue(repeatedOutcome.failure().isEmpty());
+        verify(ingestionFixture.hybridVectorService, never()).deleteByUrl(any(QdrantCollectionKind.class), anyString());
+        verify(ingestionFixture.ingestedFilePruneService, never())
+                .pruneObsoleteLocalStateAfterReplacement(anyString(), any(), any());
+        verify(ingestionFixture.fileIngestionMarkerStore, never())
+                .markFileIngested(anyString(), any(FileIngestionRecord.class));
+        verify(ingestionFixture.quarantineService, never()).quarantine(any(Path.class));
+        verify(ingestionFixture.chunkProcessingService, never())
+                .processAndStoreChunks(anyString(), anyString(), anyString(), anyString());
+    }
+
     @Test
     void shouldStopBeforeLaterFileWhenChunkStorageFails(@TempDir Path temporaryDirectory) throws IOException {
         DocumentationSource documentationSource =