diff --git a/src/components/chat-composer.test.ts b/src/components/chat-composer.test.ts
index 7041fc5..99b4a82 100644
--- a/src/components/chat-composer.test.ts
+++ b/src/components/chat-composer.test.ts
@@ -1,6 +1,13 @@
 // @vitest-environment jsdom
 import React from "react";
-import { cleanup, render, screen, within } from "@testing-library/react";
+import {
+  cleanup,
+  fireEvent,
+  render,
+  screen,
+  waitFor,
+  within,
+} from "@testing-library/react";
 import userEvent from "@testing-library/user-event";
 import { afterEach, describe, expect, it, vi } from "vitest";
 
@@ -51,7 +58,7 @@ describe("ChatComposer", () => {
     expect(onLoginClick).toHaveBeenCalledOnce();
   });
 
-  it("inserts expert templates and highlights bracket placeholders", async () => {
+  it("inserts expert templates and selects the first placeholder for replacement", async () => {
     const user = userEvent.setup();
 
     render(React.createElement(ChatComposer));
@@ -64,12 +71,71 @@ describe("ChatComposer", () => {
     const input = screen.getByPlaceholderText(
       "Ask a question about your documents…",
     ) as HTMLTextAreaElement;
+    const placeholderStart = input.value.indexOf("[Company Name]");
+    const placeholderEnd = placeholderStart + "[Company Name]".length;
+
     expect(input.value).toContain("prospectus of [Company Name]");
+    await waitFor(() => {
+      expect(input.selectionStart).toBe(placeholderStart);
+      expect(input.selectionEnd).toBe(placeholderEnd);
+    });
+    expect(screen.queryByTestId("chat-composer-highlight-layer")).toBeNull();
+
+    await user.type(input, "Acme Robotics", { skipClick: true });
+
+    expect(input.value).toContain("prospectus of Acme Robotics");
+    expect(input.value).not.toContain("[Company Name]");
+  });
+
+  it("highlights placeholders when text is not selected", async () => {
+    const user = userEvent.setup();
+
+    render(React.createElement(ChatComposer));
+
+    await user.click(screen.getByRole("button", { name: "Create" }));
+    await user.click(
+      screen.getByRole("menuitem", { name: /IPO Prospectus Risk Mining/ }),
+    );
+
+    const input = screen.getByPlaceholderText(
+      "Ask a question about your documents…",
+    ) as HTMLTextAreaElement;
+    await waitFor(() => expect(input.value).toContain("[Company Name]"));
+
+    input.setSelectionRange(input.value.length, input.value.length);
+    fireEvent.select(input);
+
     expect(screen.getByText("[Company Name]").className).toContain(
       "text-primary",
     );
   });
 
+  it("selects a placeholder with one click when the caret lands inside it", async () => {
+    const user = userEvent.setup();
+
+    render(React.createElement(ChatComposer));
+
+    await user.click(screen.getByRole("button", { name: "Create" }));
+    await user.click(
+      screen.getByRole("menuitem", {
+        name: /Earnings Call Transcript Analysis/,
+      }),
+    );
+
+    const input = screen.getByPlaceholderText(
+      "Ask a question about your documents…",
+    ) as HTMLTextAreaElement;
+    await waitFor(() => expect(input.value).toContain("[Company Name]"));
+
+    const placeholderStart = input.value.indexOf("[Company Name]");
+    const placeholderEnd = placeholderStart + "[Company Name]".length;
+    input.setSelectionRange(placeholderStart + 3, placeholderStart + 3);
+    fireEvent.click(input);
+
+    expect(input.selectionStart).toBe(placeholderStart);
+    expect(input.selectionEnd).toBe(placeholderEnd);
+  });
+
   it("renders a larger embedded composer input surface", () => {
     render(React.createElement(ChatComposer));
 
diff --git a/src/components/chat-composer.tsx b/src/components/chat-composer.tsx
index 807f298..75a9a18 100644
--- a/src/components/chat-composer.tsx
+++ b/src/components/chat-composer.tsx
@@ -5,6 +5,7 @@ import {
   useState,
   type ChangeEvent,
   type KeyboardEvent,
+  type MouseEvent,
   type ReactElement,
   type UIEvent,
 } from "react";
@@ -25,6 +26,12 @@ import { chatPromptTemplates } from "@/domains/chat/prompt-templates";
 const chatComposerId = "chat-composer";
 const placeholderPattern = /(\[[^\]\r\n]{1,80}\])/gu;
 const placeholderSegmentPattern = /^\[[^\]\r\n]{1,80}\]$/u;
+const placeholderRangePattern = /\[[^\]\r\n]{1,80}\]/gu;
+
+type TextRange = {
+  readonly start: number;
+  readonly end: number;
+};
 
 export type ChatComposerProps = {
   readonly canCreateDiagram?: boolean;
@@ -46,13 +53,16 @@ export function ChatComposer({
   onSend,
 }: ChatComposerProps): ReactElement {
   const [input, setInput] = useState("");
+  const [hasActiveTextSelection, setHasActiveTextSelection] = useState(false);
   const [textareaScrollTop, setTextareaScrollTop] = useState(0);
   const textareaRef = useRef<HTMLTextAreaElement | null>(null);
   const trimmedInput = input.trim();
   const canSend = !isDisabled && !isSending && trimmedInput.length > 0;
+  const shouldShowHighlightLayer = input.length > 0 && !hasActiveTextSelection;
 
   function handleInputChange(event: ChangeEvent<HTMLTextAreaElement>): void {
     setInput(event.target.value);
+    setHasActiveTextSelection(false);
   }
 
   function handleKeyDown(event: KeyboardEvent<HTMLTextAreaElement>): void {
@@ -73,8 +83,19 @@ export function ChatComposer({
     setInput(prompt);
     setTextareaScrollTop(0);
     requestAnimationFrame(() => {
-      textareaRef.current?.focus();
-      textareaRef.current?.setSelectionRange(prompt.length, prompt.length);
+      const textarea = textareaRef.current;
+      if (!textarea) return;
+
+      textarea.focus();
+      const placeholderRange = getFirstPlaceholderRange(prompt);
+      if (!placeholderRange) {
+        textarea.setSelectionRange(prompt.length, prompt.length);
+        setHasActiveTextSelection(false);
+        return;
+      }
+
+      textarea.setSelectionRange(placeholderRange.start, placeholderRange.end);
+      setHasActiveTextSelection(true);
     });
   }
 
@@ -82,6 +103,33 @@ export function ChatComposer({
     setTextareaScrollTop(event.currentTarget.scrollTop);
   }
 
+  function handleTextareaClick(event: MouseEvent<HTMLTextAreaElement>): void {
+    const textarea = event.currentTarget;
+    if (textarea.selectionStart !== textarea.selectionEnd) {
+      setHasActiveTextSelection(true);
+      return;
+    }
+
+    const placeholderRange = getPlaceholderRangeAtPosition(
+      textarea.value,
+      textarea.selectionStart,
+    );
+    if (!placeholderRange) {
+      setHasActiveTextSelection(false);
+      return;
+    }
+
+    textarea.setSelectionRange(placeholderRange.start, placeholderRange.end);
+    setHasActiveTextSelection(true);
+  }
+
+  function refreshTextareaSelectionState(): void {
+    const textarea = textareaRef.current;
+    setHasActiveTextSelection(
+      Boolean(textarea && textarea.selectionStart !== textarea.selectionEnd),
+    );
+  }
+
   return (
     <div
       data-testid="chat-composer"
@@ -99,9 +147,10 @@ export function ChatComposer({
       ) : (
         <>
           <div className="relative overflow-hidden bg-background">
-            {input.length > 0 && (
+            {shouldShowHighlightLayer && (
               <pre
                 aria-hidden="true"
+                data-testid="chat-composer-highlight-layer"
                 className="pointer-events-none absolute inset-0 h-[128px] min-w-0 whitespace-pre-wrap break-words border border-transparent px-4 py-3 font-sans text-sm leading-5 text-foreground sm:px-5 sm:py-4"
               >
                 <span
@@ -117,7 +166,9 @@ export function ChatComposer({
               id={chatComposerId}
               name={chatComposerId}
               className={`relative h-[128px] w-full min-w-0 resize-none border-0 bg-transparent px-4 py-3 text-sm leading-5 shadow-none transition-all placeholder:text-muted-foreground focus-visible:ring-0 sm:px-5 sm:py-4 ${
-                input.length > 0 ? "text-transparent caret-foreground" : "text-foreground"
+                shouldShowHighlightLayer
+                  ? "text-transparent caret-foreground"
+                  : "text-foreground"
               }`}
               placeholder={
                 isDisabled
@@ -127,8 +178,12 @@ export function ChatComposer({
               value={input}
               onChange={handleInputChange}
               disabled={isDisabled}
+              onBlur={() => setHasActiveTextSelection(false)}
+              onClick={handleTextareaClick}
               onKeyDown={handleKeyDown}
+              onKeyUp={refreshTextareaSelectionState}
               onScroll={handleTextareaScroll}
+              onSelect={refreshTextareaSelectionState}
             />
           </div>
           <div className="flex items-center justify-between gap-3 px-4 pb-4 sm:px-5">
@@ -239,3 +294,24 @@ function renderHighlightedInput(value: string): readonly ReactElement[] {
       return <span key={key}>{segment}</span>;
     });
 }
+
+function getFirstPlaceholderRange(value: string): TextRange | null {
+  const [firstMatch] = value.matchAll(placeholderRangePattern);
+  if (!firstMatch) return null;
+  const start = firstMatch.index;
+  return { start, end: start + firstMatch[0].length };
+}
+
+function getPlaceholderRangeAtPosition(
+  value: string,
+  position: number,
+): TextRange | null {
+  for (const match of value.matchAll(placeholderRangePattern)) {
+    const start = match.index;
+    const end = start + match[0].length;
+    if (position >= start && position <= end) {
+      return { start, end };
+    }
+  }
+  return null;
+}