diff --git a/src/application/JavaScriptApplicationService.ts b/src/application/JavaScriptApplicationService.ts
index b47b6ed5e..a7e3ecdd8 100644
--- a/src/application/JavaScriptApplicationService.ts
+++ b/src/application/JavaScriptApplicationService.ts
@@ -75,7 +75,12 @@ export const analyzeJavaScriptApplicationValidated = async (
   } catch (cause: unknown) {
     if (cause instanceof ArtifactReaderFailure)
       return err(
-        new ArtifactOperationError(OPERATION, cause.reason, cause.details),
+        new ArtifactOperationError(
+          OPERATION,
+          cause.reason,
+          cause.details,
+          cause.message,
+        ),
       );
     if (cause instanceof z.ZodError)
       return err(
diff --git a/src/artifacts/ArtifactPaths.ts b/src/artifacts/ArtifactPaths.ts
index e6dd950e9..d5ec35cb4 100644
--- a/src/artifacts/ArtifactPaths.ts
+++ b/src/artifacts/ArtifactPaths.ts
@@ -14,7 +14,7 @@ export const normalizeArtifactPath = (input: string): string => {
   )
     throw new ArtifactReaderFailure(
       "path",
-      "Artifact path is absolute or unsafe",
+      `Artifact path is absolute or unsafe: ${JSON.stringify(input)}`,
     );
   const normalized = input.normalize("NFC").replace(/\/+$/u, "");
   const parts = normalized.split("/");
@@ -23,7 +23,10 @@ export const normalizeArtifactPath = (input: string): string => {
     parts.some((part) => part === "" || part === "." || part === "..") ||
     posix.normalize(normalized) !== normalized
   )
-    throw new ArtifactReaderFailure("path", "Artifact path is not normalized");
+    throw new ArtifactReaderFailure(
+      "path",
+      `Artifact path is not normalized: ${JSON.stringify(input)}`,
+    );
   return normalized;
 };
 
@@ -45,7 +48,7 @@ export class ArtifactPathRegistry {
       if (child !== undefined && child.spelling !== part)
         throw new ArtifactReaderFailure(
           "path",
-          `Artifact path collision: ${path}`,
+          `Artifact path collision: ${path} differs only in case from ${[...parts.slice(0, index), child.spelling].join("/")}`,
         );
       if (child === undefined) {
         child = { spelling: part, kind: undefined, children: new Map() };
diff --git a/src/artifacts/ArtifactProvider.ts b/src/artifacts/ArtifactProvider.ts
index e095d0dfe..370caa1af 100644
--- a/src/artifacts/ArtifactProvider.ts
+++ b/src/artifacts/ArtifactProvider.ts
@@ -343,7 +343,12 @@ const translateFailure = (
   cause: unknown,
 ): AnalysisError => {
   if (cause instanceof ArtifactReaderFailure)
-    return new ArtifactOperationError(operation, cause.reason, cause.details);
+    return new ArtifactOperationError(
+      operation,
+      cause.reason,
+      cause.details,
+      cause.message,
+    );
   return new ArtifactOperationError(operation, "io");
 };
 
diff --git a/src/domain/analysisErrorProjection.ts b/src/domain/analysisErrorProjection.ts
index 66f432a37..f4e8b6197 100644
--- a/src/domain/analysisErrorProjection.ts
+++ b/src/domain/analysisErrorProjection.ts
@@ -216,6 +216,7 @@ const artifactStateErrorDetails = (
       operation: error.operation,
       reason: error.reason,
       ...(error.reason === "limit" ? { truncated: true } : {}),
+      ...(error.detail === undefined ? {} : { detail: error.detail }),
     };
   if (error instanceof UnknownRegistryError) return { reason: error.reason };
   if (error instanceof EvidenceFileError)
diff --git a/src/domain/artifactOperationError.ts b/src/domain/artifactOperationError.ts
index 238992196..41d482ab8 100644
--- a/src/domain/artifactOperationError.ts
+++ b/src/domain/artifactOperationError.ts
@@ -28,6 +28,8 @@ export class ArtifactOperationError extends AnalysisError {
       calculatedSha256: string | null;
       unpacked: boolean;
     }>,
+    /** The specific constraint that failed, such as the colliding path. */
+    readonly detail?: string,
   ) {
     super(
       artifactDetails === undefined
diff --git a/tests/boundary/providers/native/artifactProvider.archiveSafety.test.ts b/tests/boundary/providers/native/artifactProvider.archiveSafety.test.ts
index 3c8965328..223811110 100644
--- a/tests/boundary/providers/native/artifactProvider.archiveSafety.test.ts
+++ b/tests/boundary/providers/native/artifactProvider.archiveSafety.test.ts
@@ -96,7 +96,7 @@ describe("artifact archive safety", () => {
     expect(unsafePathError).toBeInstanceOf(ArtifactReaderFailure);
     expect(unsafePathError).toMatchObject({
       reason: "path",
-      message: "Artifact path is not normalized",
+      message: 'Artifact path is not normalized: "../escape"',
     });
     const registry = new ArtifactPathRegistry();
     registry.add("A.js", "file");
@@ -109,7 +109,7 @@ describe("artifact archive safety", () => {
     expect(collisionError).toBeInstanceOf(ArtifactReaderFailure);
     expect(collisionError).toMatchObject({
       reason: "path",
-      message: "Artifact path collision: a.js",
+      message: "Artifact path collision: a.js differs only in case from A.js",
     });
 
     for (const [filePath, childPath] of [
diff --git a/tests/boundary/providers/native/artifactProvider.failureDetail.test.ts b/tests/boundary/providers/native/artifactProvider.failureDetail.test.ts
new file mode 100644
index 000000000..bf2669583
--- /dev/null
+++ b/tests/boundary/providers/native/artifactProvider.failureDetail.test.ts
@@ -0,0 +1,35 @@
+import { join } from "node:path";
+
+import { expect, it } from "vitest";
+
+import { writeOrderedZip } from "../../../fixtures/artifactEntryOrder.js";
+import { createTestTempDirectory } from "../../../fixtures/temporaryDirectory.js";
+
+import { parseBinaryTarget } from "../../../../src/application/BinaryTargetResolver.js";
+import { ArtifactProvider } from "../../../../src/artifacts/ArtifactProvider.js";
+import { projectAnalysisError } from "../../../../src/domain/analysisErrorProjection.js";
+
+it.each([
+  [
+    ["Main.js", "main.js"],
+    "Artifact path collision: main.js differs only in case from Main.js",
+  ],
+  [["a\\b.js"], 'Artifact path is absolute or unsafe: "a\\\\b.js"'],
+] as const)(
+  "reports the failed path constraint for %j",
+  async (entries, detail) => {
+    const root = await createTestTempDirectory("rea-artifact-detail-");
+    const path = join(root, "fixture.zip");
+    await writeOrderedZip(path, entries);
+    const target = await parseBinaryTarget(path);
+    if (!target.ok) throw new Error("expected a ZIP target");
+    const result = await new ArtifactProvider()
+      .createClient(target.value)
+      .execute("inventory_artifact", {});
+    if (result.ok) throw new Error("expected the path constraint to fail");
+    expect(projectAnalysisError(result.error)).toMatchObject({
+      code: "artifact_operation_failed",
+      details: { operation: "inventory_artifact", reason: "path", detail },
+    });
+  },
+);