diff --git a/src/tui/image-attachments.test.ts b/src/tui/image-attachments.test.ts
index 87833448d..519e03264 100644
--- a/src/tui/image-attachments.test.ts
+++ b/src/tui/image-attachments.test.ts
@@ -1,8 +1,8 @@
 import { describe, expect, test } from "bun:test";
 import { deflateSync } from "node:zlib";
 import { unlink } from "node:fs/promises";
-import { tmpdir } from "node:os";
-import { join } from "node:path";
+import { homedir, tmpdir } from "node:os";
+import { join, resolve } from "node:path";
 import { defined } from "../../tests/helpers/defined.js";
 import {
   findDuplicateAttachment,
@@ -72,18 +72,69 @@ function buildTestPng(width: number, height: number): Buffer {
   ]);
 }
 
-describe("image attachment helpers", () => {
-  test("detects supported image MIME types from paths", () => {
-    expect(imageMimeTypeForPath("shot.png")).toBe("image/png");
-    expect(imageMimeTypeForPath("photo.JPEG")).toBe("image/jpeg");
-    expect(imageMimeTypeForPath("animation.gif")).toBe("image/gif");
-    expect(imageMimeTypeForPath("notes.txt")).toBeUndefined();
+describe("findImagePathMentions", () => {
+  test("preserves balanced wrappers and exact inner whitespace", () => {
+    const observed =
+      "/Users/operator/Desktop/Screenshot 2026-09-10 at 11.42.07\u202fAM.png";
+
+    expect(findImagePathMentions(`inspect '${observed}'`, "/repo")).toEqual([
+      { raw: `'${observed}'`, path: observed },
+    ]);
+    expect(
+      findImagePathMentions(
+        '"./screen (final), version; 2.png", `~/screen: final!.webp`!',
+        "/repo",
+      ),
+    ).toEqual([
+      {
+        raw: '"./screen (final), version; 2.png"',
+        path: "/repo/screen (final), version; 2.png",
+      },
+      {
+        raw: "`~/screen: final!.webp`",
+        path: join(homedir(), "screen: final!.webp"),
+      },
+    ]);
   });
 
-  test("finds image paths embedded in instructions", () => {
+  test("normalizes wrapped file URLs and keeps quoted backslashes literal", () => {
     expect(
       findImagePathMentions(
-        "what is in /tmp/Screenshot 2026-01-01.png please",
+        '`file:///tmp/my%20shot.jpeg` and "/tmp/my\\ shot.png"',
+        "/repo",
+      ),
+    ).toEqual([
+      { raw: "`file:///tmp/my%20shot.jpeg`", path: "/tmp/my shot.jpeg" },
+      { raw: '"/tmp/my\\ shot.png"', path: "/tmp/my\\ shot.png" },
+    ]);
+  });
+
+  test("preserves every unquoted terminator", () => {
+    expect(findImagePathMentions("/tmp/shot.png", "/repo")).toEqual([
+      { raw: "/tmp/shot.png", path: "/tmp/shot.png" },
+    ]);
+    for (const terminator of [
+      " ",
+      "\t",
+      "\n",
+      ")",
+      ",",
+      ".",
+      ";",
+      ":",
+      "!",
+      "?",
+    ]) {
+      expect(
+        findImagePathMentions(`/tmp/shot.png${terminator}after`, "/repo"),
+      ).toEqual([{ raw: "/tmp/shot.png", path: "/tmp/shot.png" }]);
+    }
+  });
+
+  test("preserves unquoted parsing and normalization", () => {
+    expect(
+      findImagePathMentions(
+        "what is in /tmp/Screenshot 2026-01-01.png please file:///tmp/my%20shot.jpg ./other.webp",
         "/repo",
       ),
     ).toEqual([
@@ -91,10 +142,63 @@ describe("image attachment helpers", () => {
         raw: "/tmp/Screenshot 2026-01-01.png",
         path: "/tmp/Screenshot 2026-01-01.png",
       },
+      { raw: "file:///tmp/my%20shot.jpg", path: "/tmp/my shot.jpg" },
+      { raw: "./other.webp", path: "/repo/other.webp" },
+    ]);
+    expect(findImagePathMentions("./relative path.png", "/repo")).toEqual([]);
+  });
+
+  test("bounds unmatched wrappers to their line and old unquoted boundaries", () => {
+    expect(
+      findImagePathMentions(
+        "look at '/tmp/first.png next\nthen' /tmp/second.jpg",
+        "/repo",
+      ),
+    ).toEqual([
+      { raw: "/tmp/first.png", path: "/tmp/first.png" },
+      { raw: "/tmp/second.jpg", path: "/tmp/second.jpg" },
+    ]);
+    expect(findImagePathMentions('/tmp/shot.png"', "/repo")).toEqual([]);
+    expect(findImagePathMentions('"./first.png\ncontinued"', "/repo")).toEqual([
+      { raw: "./first.png", path: resolve("/repo", "first.png") },
     ]);
+  });
+
+  test("keeps source order, deduplicates normalized paths, and rejects unsupported candidates", () => {
     expect(
-      findImagePathMentions("look at file:///tmp/my%20shot.png", "/repo"),
-    ).toEqual([{ raw: "file:///tmp/my%20shot.png", path: "/tmp/my shot.png" }]);
+      findImagePathMentions(
+        "`./first.gif` /repo/second.JPG './first.gif' image.png './bad.bmp' \"./valid.png.txt\"",
+        "/repo",
+      ),
+    ).toEqual([
+      { raw: "`./first.gif`", path: "/repo/first.gif" },
+      { raw: "/repo/second.JPG", path: "/repo/second.JPG" },
+    ]);
+  });
+
+  test("does not let contractions steal single-quoted path wrappers", () => {
+    const observed = "/tmp/Screenshot 2026-09-10 at 11.42.07\u202fAM.png";
+    expect(findImagePathMentions(`what's in '${observed}'?`, "/repo")).toEqual([
+      { raw: `'${observed}'`, path: observed },
+    ]);
+    expect(
+      findImagePathMentions(`don't use '/tmp/shot.png' please`, "/repo"),
+    ).toEqual([{ raw: "'/tmp/shot.png'", path: "/tmp/shot.png" }]);
+  });
+
+  test("does not let prose quotes invent a relative path over an absolute mention", () => {
+    expect(
+      findImagePathMentions(`He said "look at /tmp/shot.png" today`, "/repo"),
+    ).toEqual([{ raw: "/tmp/shot.png", path: "/tmp/shot.png" }]);
+  });
+});
+
+describe("image attachment helpers", () => {
+  test("detects supported image MIME types from paths", () => {
+    expect(imageMimeTypeForPath("shot.png")).toBe("image/png");
+    expect(imageMimeTypeForPath("photo.JPEG")).toBe("image/jpeg");
+    expect(imageMimeTypeForPath("animation.gif")).toBe("image/gif");
+    expect(imageMimeTypeForPath("notes.txt")).toBeUndefined();
   });
 
   test("leaves small images untouched", async () => {
diff --git a/src/tui/image-attachments.ts b/src/tui/image-attachments.ts
index ce304ba4a..1ed38a731 100644
--- a/src/tui/image-attachments.ts
+++ b/src/tui/image-attachments.ts
@@ -67,19 +67,131 @@ export function findImagePathMentions(
 ): ImagePathMention[] {
   const mentions: ImagePathMention[] = [];
   const seen = new Set<string>();
-  const pattern =
-    /file:\/\/\S+|(?:[~./]|[A-Za-z]:)[^\n\r]*?\.(?:png|jpe?g|webp|gif)(?=$|\s|[),.;:!?])/gi;
-  let match: RegExpExecArray | null;
-  while ((match = pattern.exec(text)) !== null) {
-    const raw = trimTrailingPunctuation(match[0] ?? "");
-    const path = normalizeImagePathCandidate(raw, cwd);
-    if (path === undefined || seen.has(path)) continue;
+
+  const push = (raw: string, path: string | undefined): void => {
+    if (path === undefined || seen.has(path)) return;
     seen.add(path);
     mentions.push({ raw, path });
+  };
+
+  let lineStart = 0;
+  while (lineStart <= text.length) {
+    let lineEnd = text.indexOf("\n", lineStart);
+    if (lineEnd === -1) lineEnd = text.length;
+    // Keep a lone trailing \r on CRLF out of the scan window.
+    const contentEnd =
+      lineEnd > lineStart && text[lineEnd - 1] === "\r" ? lineEnd - 1 : lineEnd;
+    scanImagePathLine(text, lineStart, contentEnd, cwd, push);
+    if (lineEnd === text.length) break;
+    lineStart = lineEnd + 1;
   }
   return mentions;
 }
 
+const WRAPPERS = new Set(["'", '"', "`"]);
+const UNQUOTED_AT =
+  /^(?:file:\/\/\S+|(?:[~./]|[A-Za-z]:)[^\n\r]*?\.(?:png|jpe?g|webp|gif)(?=$|\s|[),.;:!?]))/i;
+
+function scanImagePathLine(
+  text: string,
+  start: number,
+  end: number,
+  cwd: string,
+  push: (raw: string, path: string | undefined) => void,
+): void {
+  let i = start;
+  while (i < end) {
+    const ch = text[i];
+    if (ch === undefined) break;
+    if (WRAPPERS.has(ch)) {
+      // Contractions/possessives (`what's`, `don't`) are not quote openers.
+      if (ch === "'" && i > start && isWordChar(text[i - 1])) {
+        i += 1;
+        continue;
+      }
+      const close = text.indexOf(ch, i + 1);
+      if (close !== -1 && close < end) {
+        const inner = text.slice(i + 1, close);
+        if (looksLikeQuotedImagePath(inner)) {
+          const raw = text.slice(i, close + 1);
+          push(raw, normalizeImagePathCandidate(inner, cwd, true));
+          i = close + 1;
+          continue;
+        }
+        // Balanced quotes around prose are not path wrappers. Search inside
+        // so an absolute path can still be found, then resume after the closer.
+        scanImagePathLine(text, i + 1, close, cwd, push);
+        i = close + 1;
+        continue;
+      }
+      // Unmatched opener is not a wrapper; same-line unquoted fallback only.
+      i += 1;
+      continue;
+    }
+
+    if (canStartUnquotedPath(text, i, end)) {
+      const match = UNQUOTED_AT.exec(text.slice(i, end));
+      if (match?.[0] !== undefined) {
+        const raw = trimTrailingPunctuation(match[0]);
+        push(raw, normalizeImagePathCandidate(raw, cwd, false));
+        i += match[0].length;
+        continue;
+      }
+    }
+    i += 1;
+  }
+}
+
+function isWordChar(ch: string | undefined): boolean {
+  if (ch === undefined || ch.length !== 1) return false;
+  return (
+    (ch >= "0" && ch <= "9") ||
+    (ch >= "A" && ch <= "Z") ||
+    (ch >= "a" && ch <= "z")
+  );
+}
+
+function looksLikeQuotedImagePath(inner: string): boolean {
+  if (inner.startsWith("file://")) return true;
+  if (inner === "~" || inner.startsWith("~/") || inner.startsWith("~\\"))
+    return true;
+  if (inner.startsWith("/") || inner.startsWith("\\")) return true;
+  if (
+    inner.startsWith("./") ||
+    inner.startsWith("../") ||
+    inner.startsWith(".\\") ||
+    inner.startsWith("..\\")
+  ) {
+    return true;
+  }
+  const drive = inner[0];
+  const sep = inner[2];
+  return (
+    inner.length >= 3 &&
+    drive !== undefined &&
+    sep !== undefined &&
+    ((drive >= "A" && drive <= "Z") || (drive >= "a" && drive <= "z")) &&
+    inner[1] === ":" &&
+    (sep === "/" || sep === "\\")
+  );
+}
+
+function canStartUnquotedPath(text: string, i: number, end: number): boolean {
+  if (i >= end) return false;
+  if (text.startsWith("file://", i)) return true;
+  const ch = text[i];
+  if (ch === undefined) return false;
+  if (ch === "~" || ch === "." || ch === "/") return true;
+  if (
+    i + 1 < end &&
+    ((ch >= "A" && ch <= "Z") || (ch >= "a" && ch <= "z")) &&
+    text[i + 1] === ":"
+  ) {
+    return true;
+  }
+  return false;
+}
+
 export async function imageAttachmentFromPath(
   path: string,
 ): Promise<AttachImageResult> {
@@ -263,40 +375,44 @@ export function userRowText(
 function normalizeImagePathCandidate(
   input: string,
   cwd: string,
+  quoted: boolean,
 ): string | undefined {
-  const unquoted = unquoteShellPath(trimTrailingPunctuation(input.trim()));
-  if (unquoted === undefined) return undefined;
+  const resolved = quoted
+    ? resolveQuotedImagePath(input)
+    : resolveUnquotedImagePath(input);
+  if (resolved === undefined) return undefined;
   const expanded =
-    unquoted === "~" || unquoted.startsWith("~/")
-      ? resolve(homedir(), unquoted.slice(2))
-      : unquoted;
-  if (
-    /\s/.test(expanded) &&
-    !isAbsolute(expanded) &&
-    input[0] !== "'" &&
-    input[0] !== '"'
-  ) {
+    resolved === "~" || resolved.startsWith("~/")
+      ? resolve(homedir(), resolved.slice(2))
+      : resolved;
+  if (/\s/.test(expanded) && !isAbsolute(expanded) && !quoted) {
     return undefined;
   }
   const abs = isAbsolute(expanded) ? expanded : resolve(cwd, expanded);
   return imageMimeTypeForPath(abs) === undefined ? undefined : abs;
 }
 
-function unquoteShellPath(input: string): string | undefined {
-  if (input.startsWith("file://")) {
+function resolveQuotedImagePath(inner: string): string | undefined {
+  if (inner.startsWith("file://")) {
     try {
-      return decodeURIComponent(new URL(input).pathname);
+      return decodeURIComponent(new URL(inner).pathname);
     } catch {
       return undefined;
     }
   }
-  if (
-    (input.startsWith("'") && input.endsWith("'")) ||
-    (input.startsWith('"') && input.endsWith('"'))
-  ) {
-    return input.slice(1, -1);
+  return inner;
+}
+
+function resolveUnquotedImagePath(input: string): string | undefined {
+  const trimmed = trimTrailingPunctuation(input.trim());
+  if (trimmed.startsWith("file://")) {
+    try {
+      return decodeURIComponent(new URL(trimmed).pathname);
+    } catch {
+      return undefined;
+    }
   }
-  return input.replace(/\\([\\\s'"()])/g, "$1");
+  return trimmed.replace(/\\([\\\s'"()])/g, "$1");
 }
 
 function trimTrailingPunctuation(input: string): string {
diff --git a/src/tui/prompt-attachments.test.ts b/src/tui/prompt-attachments.test.ts
index 10b62abd4..c395d0386 100644
--- a/src/tui/prompt-attachments.test.ts
+++ b/src/tui/prompt-attachments.test.ts
@@ -43,6 +43,20 @@ describe("ingestPathMentions", () => {
     expect(result.attachments).toHaveLength(1);
   });
 
+  test("replaces the full wrapped token including quotes", async () => {
+    const load = async (path: string): Promise<AttachImageResult> => ({
+      ok: true,
+      attachment: { ...attachment("shot.png"), path },
+    });
+    const result = await ingestPathMentions(
+      "look at '/tmp/shot.png' please",
+      "/repo",
+      load,
+    );
+    expect(result.text).toBe("look at [Attached image: shot.png] please");
+    expect(result.attachments).toHaveLength(1);
+  });
+
   test("keeps the raw path when loading fails", async () => {
     const load = async (): Promise<AttachImageResult> => ({
       ok: false,