diff --git a/apps/mobile/src/lib/enrichedLinkPresentation.test.ts b/apps/mobile/src/lib/enrichedLinkPresentation.test.ts
index 4dd5ecbd08317..771674cc4eff6 100644
--- a/apps/mobile/src/lib/enrichedLinkPresentation.test.ts
+++ b/apps/mobile/src/lib/enrichedLinkPresentation.test.ts
@@ -34,6 +34,8 @@ describe("Enriched link presentation", () => {
       "https://example.com/app.tsx",
       "x + y",
       "README.md",
+      "Dockerfile",
+      "docker/Dockerfiles",
       "/app/settings",
     ]) {
       expect(ENRICHED_INLINE_FILE_LINK_REGEX.test(text), text).toBe(false);
diff --git a/apps/mobile/src/lib/enrichedLinkPresentation.ts b/apps/mobile/src/lib/enrichedLinkPresentation.ts
index 5d2e9431339d1..f31d8659b6614 100644
--- a/apps/mobile/src/lib/enrichedLinkPresentation.ts
+++ b/apps/mobile/src/lib/enrichedLinkPresentation.ts
@@ -17,6 +17,7 @@ import {
   parseComposerContextHref,
 } from "@t3tools/shared/composerContextReferences";
 import { hasThreadLinks, parseThreadLinkHref } from "@t3tools/shared/threadLinks";
+import { EXTENSIONLESS_FILE_NAMES } from "@t3tools/shared/markdownLinks";
 
 export function enrichedContextLinkPresentation(
   href: string,
@@ -91,8 +92,14 @@ export function enrichedLinkVariantPattern(url: string) {
   return `^${url.replace(/[.*+?^${}()|[\]\\]/g, "\\$&")}$`;
 }
 
-export const ENRICHED_INLINE_FILE_LINK_REGEX =
-  /^(?!\S*:\/\/)(?:(?:\.{1,2}[\\/]|~[\\/]|\/(?:Users|home|tmp|var|etc|opt|mnt|Volumes|private|root|usr|bin|sbin|lib|lib64|srv|dev|proc|sys|run|boot|media|workspace|workspaces)\/|[A-Za-z]:[\\/])[^\s`]+|(?:[\p{L}\p{M}\p{N}._-]+[\\/])+[\p{L}\p{M}\p{N}._-]+\.[A-Za-z0-9_-]+(?::\d+(?::\d+|-\d+)?)?|[\p{L}\p{M}\p{N}._-]+\.[A-Za-z0-9_-]+:\d+(?::\d+|-\d+)?)$/u;
+const EXTENSIONLESS_FILE_NAME_PATTERN = [...EXTENSIONLESS_FILE_NAMES]
+  .map((name) => name.replace(/[.*+?^${}()|[\]\\]/g, "\\$&"))
+  .join("|");
+
+export const ENRICHED_INLINE_FILE_LINK_REGEX = new RegExp(
+  String.raw`^(?!\S*:\/\/)(?:(?:\.{1,2}[\\/]|~[\\/]|\/(?:Users|home|tmp|var|etc|opt|mnt|Volumes|private|root|usr|bin|sbin|lib|lib64|srv|dev|proc|sys|run|boot|media|workspace|workspaces)\/|[A-Za-z]:[\\/])[^\s\x60]+|(?:[\p{L}\p{M}\p{N}._-]+[\\/])+(?:[\p{L}\p{M}\p{N}._-]+\.[A-Za-z0-9_-]+|(?:${EXTENSIONLESS_FILE_NAME_PATTERN}))(?::\d+(?::\d+|-\d+)?)?|[\p{L}\p{M}\p{N}._-]+\.[A-Za-z0-9_-]+:\d+(?::\d+|-\d+)?)$`,
+  "u",
+);
 
 export function enrichedSkillLinkRegex(skills?: ReadonlyArray<SelectableMarkdownSkill>) {
   const names = [...new Set(skills?.map((skill) => skill.name) ?? [])].filter(Boolean);
diff --git a/apps/mobile/src/lib/markdownInlineFileLinks.test.ts b/apps/mobile/src/lib/markdownInlineFileLinks.test.ts
index e2d81cf869561..3de6590dc7a4b 100644
--- a/apps/mobile/src/lib/markdownInlineFileLinks.test.ts
+++ b/apps/mobile/src/lib/markdownInlineFileLinks.test.ts
@@ -93,7 +93,13 @@ describe("inline code that names a file", () => {
     expect(rewrite("See `src/math.ts:2` and `./README.md`.")).toBe(
       "See [src/math.ts:2](<src/math.ts:2>) and [./README.md](<./README.md>).",
     );
-    for (const path of ["src/數學.ts:2", "數學/math.ts:2", "數學.ts:2", "src/數學.ts:2-4"]) {
+    for (const path of [
+      "src/數學.ts:2",
+      "數學/math.ts:2",
+      "數學.ts:2",
+      "src/數學.ts:2-4",
+      "docker/Dockerfile",
+    ]) {
       expect(rewrite(`See \`${path}\`.`), path).toBe(`See [${path}](<${path}>).`);
     }
   });
diff --git a/packages/shared/src/markdownLinks.test.ts b/packages/shared/src/markdownLinks.test.ts
index 74c4236c53c8f..76699b40d7a95 100644
--- a/packages/shared/src/markdownLinks.test.ts
+++ b/packages/shared/src/markdownLinks.test.ts
@@ -32,6 +32,7 @@ describe("inlineCodeFilePathCandidate", () => {
     ["origin/main", null],
     ["z-ai/glm-5.3", null],
     ["share/man/ls.1", "share/man/ls.1"],
+    ["docker/Dockerfile", "docker/Dockerfile"],
     ["src/main.ts/", null],
     ["./patches/", "./patches/"],
     // regression: #30757 an agent's shortened path is not a file
diff --git a/packages/shared/src/markdownLinks.ts b/packages/shared/src/markdownLinks.ts
index 8cc537194e194..0ae35231179e1 100644
--- a/packages/shared/src/markdownLinks.ts
+++ b/packages/shared/src/markdownLinks.ts
@@ -68,7 +68,7 @@ const POSIX_FILE_ROOT_PREFIXES = [
   "/workspaces/",
 ] as const;
 
-const EXTENSIONLESS_FILE_NAMES = new Set([
+export const EXTENSIONLESS_FILE_NAMES: ReadonlySet<string> = new Set([
   "Makefile",
   "makefile",
   "GNUmakefile",
@@ -202,7 +202,7 @@ export function inlineCodeFilePathCandidate(codeText: string): string | null {
         .at(-1) ?? "";
     if (VERSION_SUFFIX_PATTERN.test(basename)) return null;
     if (!FILE_EXTENSION_PATTERN.test(basename)) {
-      if (!hasPosition) return null;
+      if (!hasPosition) return EXTENSIONLESS_FILE_NAMES.has(basename) ? candidate : null;
       // A `:line` suffix alone does not make `I/W217:220` a file reference.
       if (
         withoutPosition.includes("/") &&