diff --git a/apps/web/src/markdown-clipboard.test.ts b/apps/web/src/markdown-clipboard.test.ts
new file mode 100644
index 00000000000..7265e8b6043
--- /dev/null
+++ b/apps/web/src/markdown-clipboard.test.ts
@@ -0,0 +1,95 @@
+import { afterEach, beforeEach, describe, expect, it, vi } from "vite-plus/test";
+
+import { serializeRenderedMarkdownFragment } from "./markdown-clipboard";
+
+const TEXT_NODE = 3;
+const ELEMENT_NODE = 1;
+
+class FakeText {
+  readonly nodeType = TEXT_NODE;
+  readonly childNodes: ReadonlyArray<never> = [];
+
+  constructor(readonly textContent: string) {}
+}
+
+class FakeElement {
+  readonly nodeType = ELEMENT_NODE;
+  readonly childNodes: Array<FakeElement | FakeText> = [];
+  readonly classList = {
+    contains: (name: string) => this.classNames.includes(name),
+  };
+
+  constructor(
+    readonly tagName: string,
+    private readonly classNames: ReadonlyArray<string> = [],
+  ) {}
+
+  get localName(): string {
+    return this.tagName.toLowerCase();
+  }
+
+  get textContent(): string {
+    return this.childNodes.map((child) => child.textContent).join("");
+  }
+
+  append(...children: Array<FakeElement | FakeText>): this {
+    this.childNodes.push(...children);
+    return this;
+  }
+
+  getAttribute(): string | null {
+    return null;
+  }
+
+  hasAttribute(): boolean {
+    return false;
+  }
+}
+
+function asNode(element: FakeElement): Node {
+  return element as unknown as Node;
+}
+
+function shikiCodeLine(text: string): FakeElement {
+  const token = new FakeElement("SPAN").append(new FakeText(text));
+  return new FakeElement("SPAN", ["line"]).append(token);
+}
+
+describe("serializeRenderedMarkdownFragment", () => {
+  beforeEach(() => {
+    vi.stubGlobal("Node", { TEXT_NODE, ELEMENT_NODE });
+  });
+
+  afterEach(() => {
+    vi.unstubAllGlobals();
+  });
+
+  it("wraps inline code in backticks", () => {
+    const paragraph = new FakeElement("P").append(
+      new FakeText("run "),
+      new FakeElement("CODE").append(new FakeText("git status")),
+      new FakeText(" first"),
+    );
+    const container = new FakeElement("DIV").append(paragraph);
+
+    expect(serializeRenderedMarkdownFragment(asNode(container))).toBe("run `git status` first");
+  });
+
+  it("keeps a highlighted block code selection plain when its pre wrapper is outside the range", () => {
+    const code = new FakeElement("CODE").append(
+      shikiCodeLine("git show-ref --verify refs/remotes/origin/opt/deploy/dev"),
+    );
+    const container = new FakeElement("DIV").append(code);
+
+    expect(serializeRenderedMarkdownFragment(asNode(container))).toBe(
+      "git show-ref --verify refs/remotes/origin/opt/deploy/dev",
+    );
+  });
+
+  it("keeps a multi-line code selection plain instead of inline-wrapping it", () => {
+    const code = new FakeElement("CODE").append(new FakeText("first line\nsecond line"));
+    const container = new FakeElement("DIV").append(code);
+
+    expect(serializeRenderedMarkdownFragment(asNode(container))).toBe("first line\nsecond line");
+  });
+});
diff --git a/apps/web/src/markdown-clipboard.ts b/apps/web/src/markdown-clipboard.ts
index 86965eebfa9..50a68562699 100644
--- a/apps/web/src/markdown-clipboard.ts
+++ b/apps/web/src/markdown-clipboard.ts
@@ -37,6 +37,22 @@ function wrapInlineMarker(content: string, marker: string): string {
   return `${match?.[1] ?? ""}${marker}${core}${marker}${match?.[3] ?? ""}`;
 }
 
+/**
+ * A code element whose pre wrapper fell outside the copied range is still
+ * block code, recognizable by its highlighter line spans or embedded
+ * newlines. Wrapping it like inline code produces backtick-surrounded
+ * shell commands on paste.
+ */
+function isBlockCodeElement(element: Element, content: string): boolean {
+  if (content.includes("\n")) return true;
+  for (const child of element.childNodes) {
+    if (child.nodeType === Node.ELEMENT_NODE && (child as Element).classList.contains("line")) {
+      return true;
+    }
+  }
+  return false;
+}
+
 function wrapInlineCode(code: string): string {
   const longestRun = [...(code.match(/`+/g) ?? [])].reduce(
     (max, run) => Math.max(max, run.length),
@@ -201,8 +217,10 @@ function serializeNode(node: Node): string {
       return `${serializeChildren(element).trim()}\n\n`;
     case "PRE":
       return serializeCodeBlock(element);
-    case "CODE":
-      return wrapInlineCode(element.textContent ?? "");
+    case "CODE": {
+      const content = element.textContent ?? "";
+      return isBlockCodeElement(element, content) ? content : wrapInlineCode(content);
+    }
     case "STRONG":
     case "B":
       return wrapInlineMarker(serializeChildren(element), "**");