diff --git a/packages/app/e2e/browser/file-editing.spec.ts b/packages/app/e2e/browser/file-editing.spec.ts
index da729381d2..0d63336d59 100644
--- a/packages/app/e2e/browser/file-editing.spec.ts
+++ b/packages/app/e2e/browser/file-editing.spec.ts
@@ -105,6 +105,37 @@ async function seedAgentWithFileLink(input: LinkedFile) {
 }
 
 test.describe("CodeMirror workspace file editing", () => {
+  test("opens explicit screenshot links and explains missing files", async ({ page }) => {
+    const session = await seedMockAgentWorkspace({
+      repoPrefix: "screenshot-markdown-link-",
+      title: "Screenshot file links",
+      initialPrompt: "Show screenshots",
+      featureValues: {
+        mockAssistantResponse:
+          "[Capture](.dev/tablet-review/capture.png) [Missing capture](.dev/tablet-review/missing.png)",
+      },
+    });
+    try {
+      await mkdir(path.join(session.cwd, ".dev/tablet-review"), { recursive: true });
+      await writeFile(path.join(session.cwd, ".dev/tablet-review/capture.png"), RED_PIXEL);
+      await openAgentRoute(page, session);
+      await test.step("Open the linked screenshot", async () => {
+        await openAssistantMarkdownLink(page, "Capture");
+        await expectFileTabOpen(page, ".dev/tablet-review/capture.png");
+        await expect(page.getByTestId("image-file-preview-canvas")).toBeVisible();
+      });
+      await test.step("Explain why the missing screenshot cannot open", async () => {
+        await returnToAssistant(page, session.agentId);
+        await openAssistantMarkdownLink(page, "Missing capture");
+        await expectFileTabOpen(page, ".dev/tablet-review/missing.png");
+        await expect(page.getByText(/ENOENT/)).toBeVisible();
+        await expect(page.getByRole("button", { name: "Retry", exact: true })).toBeVisible();
+      });
+    } finally {
+      await session.cleanup();
+    }
+  });
+
   test("opens the non-ASCII file named by an assistant markdown link", async ({ page }) => {
     const session = await seedMockAgentWorkspace({
       repoPrefix: "encoded-markdown-link-",
diff --git a/packages/app/src/assistant-file-links/parse.ts b/packages/app/src/assistant-file-links/parse.ts
index c195a277cf..4fb41a72ca 100644
--- a/packages/app/src/assistant-file-links/parse.ts
+++ b/packages/app/src/assistant-file-links/parse.ts
@@ -23,6 +23,8 @@ const INLINE_PAREN_LINE_SUFFIX = /^(.+?)\(([0-9]+)(?:,[0-9]+)?(?:-([0-9]+)(?:,[0
 const INLINE_WORD_LINE_SUFFIX = /^(.+?)\s+lines?\s+([0-9]+)(?:-([0-9]+))?$/i;
 export interface AssistantHrefParseOptions {
   workspaceRoot?: string;
+  /** Authored links identify a file; only inferred text needs filename heuristics. */
+  explicitLink?: boolean;
   /**
    * True only when `value` is a markdown href — the renderer percent-encodes
    * non-ASCII and space characters, so the path must be decoded. Raw path
@@ -30,8 +32,6 @@ export interface AssistantHrefParseOptions {
    * send a real file named `my%20file.md` to `my file.md`.
    */
   decodeHref?: boolean;
-  /** Explicit Markdown links can name nested folders without a filename extension. */
-  allowExtensionlessNestedPaths?: boolean;
 }
 
 export type AssistantFileLinkClassification =
@@ -236,7 +236,7 @@ export function classifyAssistantFileLink(
     return null;
   }
 
-  if (isAmbiguousWorkspaceCandidate(trimmed, target, options)) {
+  if (!options.explicitLink && isAmbiguousWorkspaceCandidate(trimmed, target, options)) {
     return {
       kind: "ambiguousFileCandidate",
       target,
@@ -280,7 +280,7 @@ export function parseAssistantFileLink(
   const relativeTarget = parseWorkspaceRelativeFileLink(trimmed, {
     workspaceRoot: options.workspaceRoot,
     decodeHref: options.decodeHref,
-    allowExtensionlessNestedPaths: options.allowExtensionlessNestedPaths,
+    explicitLink: options.explicitLink,
   });
   if (relativeTarget) {
     return relativeTarget;
@@ -414,7 +414,7 @@ function parseWorkspaceRelativeFileLink(
 
 function parseLocalPathParts(
   value: string,
-  options: Pick<AssistantHrefParseOptions, "decodeHref" | "allowExtensionlessNestedPaths"> = {},
+  options: Pick<AssistantHrefParseOptions, "decodeHref" | "explicitLink"> = {},
 ): {
   path: string;
   lines: Pick<InlinePathTarget, "lineStart" | "lineEnd">;
@@ -440,7 +440,7 @@ function parseLocalPathParts(
     if (options.decodeHref) {
       pathPart = safeDecodeURIComponent(pathPart);
     }
-    if (!isPlausibleAssistantLocalPath(pathPart, options)) {
+    if (!options.explicitLink && !isPlausibleAssistantLocalPath(pathPart)) {
       return null;
     }
     return {
@@ -461,7 +461,7 @@ function parseLocalPathParts(
     decodedBeforeHash = safeDecodeURIComponent(beforeHash);
   }
   const plausiblePath = parseInlinePathToken(decodedBeforeHash)?.path ?? decodedBeforeHash;
-  if (!isPlausibleAssistantLocalPath(plausiblePath, options)) {
+  if (!options.explicitLink && !isPlausibleAssistantLocalPath(plausiblePath)) {
     return null;
   }
 
@@ -586,10 +586,7 @@ function getHeuristicLocalPath(value: string): string | null {
   return beforeHash;
 }
 
-function isPlausibleAssistantLocalPath(
-  pathValue: string,
-  options: Pick<AssistantHrefParseOptions, "allowExtensionlessNestedPaths"> = {},
-): boolean {
+function isPlausibleAssistantLocalPath(pathValue: string): boolean {
   const normalized = normalizePathToken(pathValue);
   if (!normalized) {
     return false;
@@ -613,10 +610,7 @@ function isPlausibleAssistantLocalPath(
 
   if (segments.length > 1) {
     const lastSegment = segments[segments.length - 1];
-    return (
-      !isDomainLikePathSegment(firstSegment) &&
-      (options.allowExtensionlessNestedPaths === true || isPlausibleAssistantFileName(lastSegment))
-    );
+    return !isDomainLikePathSegment(firstSegment) && isPlausibleAssistantFileName(lastSegment);
   }
 
   return isPlausibleAssistantFileName(firstSegment);
diff --git a/packages/app/src/assistant-file-links/resolver.test.ts b/packages/app/src/assistant-file-links/resolver.test.ts
index 854c358627..96884c21c7 100644
--- a/packages/app/src/assistant-file-links/resolver.test.ts
+++ b/packages/app/src/assistant-file-links/resolver.test.ts
@@ -50,7 +50,7 @@ it.each([{ markup: "linkify" }, { sourceInfo: "auto" }])(
   },
 );
 
-it.each(["example.com/guides", "docs/guides?view=all"])(
+it.each(["docs/guides?view=all"])(
   "does not turn URL-like hrefs into workspace paths: %s",
   (href) => {
     expect(classifyForResolution({ href }, CONTEXT)).toEqual({
@@ -60,6 +60,21 @@ it.each(["example.com/guides", "docs/guides?view=all"])(
   },
 );
 
+it.each([
+  ".dev/tablet-review/tablet-agent-draft.png",
+  "images/capture.jpg",
+  "downloads/archive.custom",
+  "assets/LICENSE",
+  "example.com/guides",
+  "capture.png",
+  "missing.png",
+])("opens explicit file link %s without filename guessing", (href) => {
+  expect(classifyForResolution({ href }, CONTEXT)).toMatchObject({
+    kind: "resolved",
+    value: { kind: "file", target: { path: `${CONTEXT.workspaceRoot}/${href}` } },
+  });
+});
+
 it("opens the existing non-ASCII file named by a rendered markdown link", async () => {
   const workspaceRoot = await mkdtemp(path.join(tmpdir(), "assistant-file-link-"));
   try {
diff --git a/packages/app/src/assistant-file-links/resolver.ts b/packages/app/src/assistant-file-links/resolver.ts
index 59057ba0ca..be012077a3 100644
--- a/packages/app/src/assistant-file-links/resolver.ts
+++ b/packages/app/src/assistant-file-links/resolver.ts
@@ -117,7 +117,7 @@ export function classifyForResolution(
   const classification = classifyAssistantFileLink(token, {
     workspaceRoot: context.workspaceRoot,
     decodeHref: tokenInfo.fromHref,
-    allowExtensionlessNestedPaths: tokenInfo.fromHref && !isLinkifiedSource(source),
+    explicitLink: source.sourceType !== "inline-code" && !isLinkifiedSource(source),
   });
   if (!classification) {
     return { kind: "resolved", value: { kind: "ignored" } };