diff --git a/e2e/extension.spec.ts b/e2e/extension.spec.ts
index 0888763..3ee058b 100644
--- a/e2e/extension.spec.ts
+++ b/e2e/extension.spec.ts
@@ -286,6 +286,68 @@ test.describe("Slash Commands", () => {
 
     await context.close();
   });
+
+  test("hint tooltip appears on focus and hides on blur", async () => {
+    const context = await chromium.launch({ headless: false });
+    const page = await context.newPage();
+
+    await page.goto(`http://localhost:${testServer.port}/`);
+    await page.waitForLoadState("domcontentloaded");
+    await injectContentScript(page);
+    await page.waitForTimeout(500);
+
+    const textarea = page.locator("#test-textarea");
+    await expect(textarea).toBeVisible();
+
+    // Focus the textarea - tooltip should appear
+    await textarea.click();
+    await page.waitForTimeout(200);
+
+    const tooltip = page.locator("#slashPaletteHint");
+    await expect(tooltip).toBeVisible({ timeout: 2000 });
+
+    // Tooltip should contain the "//" hint text
+    const tooltipText = await tooltip.textContent();
+    expect(tooltipText).toContain("//");
+
+    // Blur the textarea - tooltip should hide
+    await page.keyboard.press("Tab");
+    await page.waitForTimeout(200);
+    await expect(tooltip).not.toBeVisible();
+
+    await context.close();
+  });
+
+  test("hint tooltip hides when picker opens", async () => {
+    const context = await chromium.launch({ headless: false });
+    const page = await context.newPage();
+
+    await page.goto(`http://localhost:${testServer.port}/`);
+    await page.waitForLoadState("domcontentloaded");
+    await injectContentScript(page);
+    await page.waitForTimeout(500);
+
+    const textarea = page.locator("#test-textarea");
+    await textarea.click();
+    await page.waitForTimeout(200);
+
+    // Tooltip should be visible after focus
+    const tooltip = page.locator("#slashPaletteHint");
+    await expect(tooltip).toBeVisible({ timeout: 2000 });
+
+    // Type // to open picker
+    await textarea.fill("//");
+    await page.waitForTimeout(500);
+
+    // Picker should be visible
+    const picker = page.locator("#slashPalettePicker");
+    await expect(picker).toBeVisible({ timeout: 3000 });
+
+    // Tooltip should be hidden
+    await expect(tooltip).not.toBeVisible();
+
+    await context.close();
+  });
 });
 
 test.describe("Options Page - Giphy Image Settings", () => {
diff --git a/src/content/hint-tooltip.ts b/src/content/hint-tooltip.ts
new file mode 100644
index 0000000..3ec2b42
--- /dev/null
+++ b/src/content/hint-tooltip.ts
@@ -0,0 +1,73 @@
+/**
+ * Hint tooltip shown near qualifying markdown textareas.
+ * Displays a small indicator hinting to type "//" to open the command list.
+ */
+
+import { isDarkMode, fontSystemUi, fontSansSerif } from "../utils/theme.ts"
+import { COMMAND_PREFIX } from "../utils/command-prefix.ts"
+
+let tooltipEl: HTMLElement | null = null
+
+function applyTooltipStyles(el: HTMLElement): void {
+  const dark = isDarkMode()
+  el.style.position = "fixed"
+  el.style.zIndex = "999998"
+  el.style.fontSize = "12px"
+  el.style.padding = "3px 7px"
+  el.style.borderRadius = "4px"
+  el.style.pointerEvents = "none"
+  el.style.whiteSpace = "nowrap"
+  el.style.fontFamily = fontSystemUi() + ", " + fontSansSerif()
+  el.style.color = dark ? "#8d96a0" : "#656d76"
+  el.style.border = `1px solid ${dark ? "#3d444d" : "#d0d7de"}`
+  el.style.backgroundColor = dark ? "#161b22" : "#ffffff"
+  el.style.boxShadow = dark ? "0 2px 8px rgba(1,4,9,0.4)" : "0 2px 8px rgba(140,149,159,0.15)"
+}
+
+function ensureTooltip(): HTMLElement {
+  if (!tooltipEl || !document.body.contains(tooltipEl)) {
+    const el = document.createElement("div")
+    el.id = "slashPaletteHint"
+    el.textContent = `Type ${COMMAND_PREFIX} for commands`
+    el.style.display = "none"
+    applyTooltipStyles(el)
+    document.body.appendChild(el)
+    tooltipEl = el
+  }
+  return tooltipEl
+}
+
+function positionTooltip(field: HTMLTextAreaElement): void {
+  const el = tooltipEl
+  if (!el) return
+  const rect = field.getBoundingClientRect()
+  const elWidth = el.offsetWidth || 160
+  const left = Math.max(0, rect.right - elWidth)
+  const top = rect.bottom + 4
+  el.style.left = `${left}px`
+  el.style.top = `${top}px`
+}
+
+export function showHintTooltip(field: HTMLTextAreaElement): void {
+  const el = ensureTooltip()
+  applyTooltipStyles(el)
+  el.style.display = "block"
+  positionTooltip(field)
+}
+
+export function hideHintTooltip(): void {
+  if (tooltipEl) {
+    tooltipEl.style.display = "none"
+  }
+}
+
+export function repositionHintTooltip(field: HTMLTextAreaElement): void {
+  if (!tooltipEl || tooltipEl.style.display === "none") return
+  positionTooltip(field)
+}
+
+export function refreshHintTooltipTheme(): void {
+  if (tooltipEl && tooltipEl.style.display !== "none") {
+    applyTooltipStyles(tooltipEl)
+  }
+}
diff --git a/src/content/index.ts b/src/content/index.ts
index 17b74db..06046aa 100644
--- a/src/content/index.ts
+++ b/src/content/index.ts
@@ -23,6 +23,12 @@ import {
   moveSelectionGrid,
   applyPickerStyles,
 } from "./picker/index.ts"
+import {
+  showHintTooltip,
+  hideHintTooltip,
+  repositionHintTooltip,
+  refreshHintTooltipTheme,
+} from "./hint-tooltip.ts"
 
 // Import commands to register them
 import "./commands/giphy/index.ts"
@@ -119,6 +125,7 @@ async function handleCommandInput(
   state.activeCommand = cmdName
   setHeader("Slash Palette", COMMAND_PREFIX + cmdName + (query ? " " + query : ""))
 
+  hideHintTooltip()
   showPicker(field)
   positionPickerAtCaret(field)
 
@@ -303,6 +310,9 @@ function attachToField(field: HTMLTextAreaElement): void {
   ;(field as unknown as { __slashPaletteBound: boolean }).__slashPaletteBound = true
 
   field.addEventListener("input", () => handleFieldInput(field))
+  field.addEventListener("focus", () => {
+    if (!isPickerVisible()) showHintTooltip(field)
+  })
   field.addEventListener("keyup", (ev) => {
     // Skip action keys that are handled elsewhere
     if (ev.key === "Escape") return
@@ -336,10 +346,12 @@ function attachToField(field: HTMLTextAreaElement): void {
   })
   field.addEventListener("scroll", () => {
     if (isPickerVisible()) positionPickerAtCaret(field)
+    repositionHintTooltip(field)
   })
   field.addEventListener("keydown", (ev) => onFieldKeyDown(ev, field))
 
   field.addEventListener("blur", () => {
+    hideHintTooltip()
     setTimeout(() => {
       // Never hide while settings panel is open - user is interacting with controls
       if (state.showingSettings) return
@@ -420,6 +432,7 @@ function boot(): void {
       if (isPickerVisible() && state.activeField) {
         positionPickerAtCaret(state.activeField)
       }
+      if (state.activeField) repositionHintTooltip(state.activeField)
     },
     { passive: true }
   )
@@ -428,13 +441,16 @@ function boot(): void {
     if (isPickerVisible() && state.activeField) {
       positionPickerAtCaret(state.activeField)
     }
+    if (state.activeField) repositionHintTooltip(state.activeField)
   })
 
   // Handle theme changes
   onThemeChange(() => {
-    if (!isPickerVisible()) return
-    if (state.pickerEl) applyPickerStyles(state.pickerEl)
-    refreshSelectionStyles()
+    if (isPickerVisible()) {
+      if (state.pickerEl) applyPickerStyles(state.pickerEl)
+      refreshSelectionStyles()
+    }
+    refreshHintTooltipTheme()
   })
 }