diff --git a/bin/cli/tray/icon.ico b/bin/cli/tray/icon.ico
new file mode 100644
index 0000000000..f0891cfc79
Binary files /dev/null and b/bin/cli/tray/icon.ico differ
diff --git a/bin/cli/tray/icon.png b/bin/cli/tray/icon.png
index 4e4abe2b78..508f949e16 100644
Binary files a/bin/cli/tray/icon.png and b/bin/cli/tray/icon.png differ
diff --git a/changelog.d/fixes/13535-windows-tray-icon-contrast.md b/changelog.d/fixes/13535-windows-tray-icon-contrast.md
new file mode 100644
index 0000000000..8c4aa21333
--- /dev/null
+++ b/changelog.d/fixes/13535-windows-tray-icon-contrast.md
@@ -0,0 +1 @@
+- **fix(cli):** redraw the CLI/Electron system tray icon with a dark outline and ship a native multi-res `icon.ico` so it is no longer a pure-white, nearly invisible glyph on the Windows light-theme taskbar and hidden-icons flyout (#13535) — thanks @ProphetOfDoom-PoD
diff --git a/electron/assets/tray-icon.png b/electron/assets/tray-icon.png
index 4e4abe2b78..508f949e16 100644
Binary files a/electron/assets/tray-icon.png and b/electron/assets/tray-icon.png differ
diff --git a/tests/unit/tray-icon-contrast.test.ts b/tests/unit/tray-icon-contrast.test.ts
new file mode 100644
index 0000000000..d9ebca19cf
--- /dev/null
+++ b/tests/unit/tray-icon-contrast.test.ts
@@ -0,0 +1,104 @@
+// Regression guard for #13535: the Windows CLI system tray icon must contain a dark
+// outline/stroke so it stays visible against the light-theme taskbar/hidden-icons
+// background. Windows' NotifyIcon paints bitmap pixel colors literally — unlike macOS
+// there is no "template image" auto-tinting — so a pure-white glyph with no outline is
+// effectively invisible there. See bin/cli/tray/tray.ts::getIconPath() (prefers icon.ico
+// on win32, falling back to icon.png) and electron/main.js (darwin-only setTemplateImage).
+import { test } from "node:test";
+import assert from "node:assert/strict";
+import { readFileSync, existsSync } from "node:fs";
+import { join, dirname } from "node:path";
+import { fileURLToPath } from "node:url";
+import sharp from "sharp";
+
+const repoRoot = dirname(dirname(dirname(fileURLToPath(import.meta.url))));
+const ICON_PNG_PATH = join(repoRoot, "bin", "cli", "tray", "icon.png");
+const ICON_ICO_PATH = join(repoRoot, "bin", "cli", "tray", "icon.ico");
+const ELECTRON_TRAY_ICON_PATH = join(repoRoot, "electron", "assets", "tray-icon.png");
+
+// Windows 11 Fluent "hidden icons" overflow flyout / light-theme taskbar background.
+const LIGHT_BG = { r: 243, g: 243, b: 243 };
+// A representative dark-theme taskbar background.
+const DARK_BG = { r: 32, g: 32, b: 32 };
+
+function relativeLuminance({ r, g, b }: { r: number; g: number; b: number }): number {
+  const lin = (c: number) => {
+    const s = c / 255;
+    return s <= 0.03928 ? s / 12.92 : Math.pow((s + 0.055) / 1.055, 2.4);
+  };
+  const [rl, gl, bl] = [lin(r), lin(g), lin(b)];
+  return 0.2126 * rl + 0.7152 * gl + 0.0722 * bl;
+}
+
+function contrastRatio(
+  a: { r: number; g: number; b: number },
+  b: { r: number; g: number; b: number }
+): number {
+  const la = relativeLuminance(a);
+  const lb = relativeLuminance(b);
+  const [lighter, darker] = la >= lb ? [la, lb] : [lb, la];
+  return (lighter + 0.05) / (darker + 0.05);
+}
+
+async function assertHasVisibleContrastAgainstBothThemes(iconPath: string, label: string) {
+  const raw = readFileSync(iconPath);
+  const { data, info } = await sharp(raw).ensureAlpha().raw().toBuffer({ resolveWithObject: true });
+  assert.equal(info.channels, 4, `expected RGBA after ensureAlpha() for ${label}`);
+
+  let opaqueCount = 0;
+  let nonWhiteOpaqueCount = 0;
+  let bestContrastOnLight = 0;
+  let bestContrastOnDark = 0;
+
+  for (let i = 0; i < data.length; i += 4) {
+    const r = data[i];
+    const g = data[i + 1];
+    const b = data[i + 2];
+    const a = data[i + 3];
+    if (a < 128) continue;
+    opaqueCount++;
+    if (!(r === 255 && g === 255 && b === 255)) nonWhiteOpaqueCount++;
+    const ratioLight = contrastRatio({ r, g, b }, LIGHT_BG);
+    if (ratioLight > bestContrastOnLight) bestContrastOnLight = ratioLight;
+    const ratioDark = contrastRatio({ r, g, b }, DARK_BG);
+    if (ratioDark > bestContrastOnDark) bestContrastOnDark = ratioDark;
+  }
+
+  assert.ok(opaqueCount > 0, `${label} has no opaque pixels at all — nothing would render`);
+  assert.ok(
+    nonWhiteOpaqueCount > 0,
+    `${label}'s glyph is pure-white-only (0 non-white opaque pixels out of ${opaqueCount}) — ` +
+      `no outline/stroke exists to provide contrast on a light background (bug #13535)`
+  );
+  assert.ok(
+    bestContrastOnLight >= 3,
+    `${label}'s best pixel contrast against the Windows light tray background (#F3F3F3) is only ` +
+      `${bestContrastOnLight.toFixed(3)}:1, below the WCAG 3:1 UI-component minimum (bug #13535)`
+  );
+  assert.ok(
+    bestContrastOnDark >= 3,
+    `${label}'s best pixel contrast against a dark tray background (#202020) is only ` +
+      `${bestContrastOnDark.toFixed(3)}:1, below the WCAG 3:1 UI-component minimum (bug #13535)`
+  );
+}
+
+test("icon.ico now ships next to icon.png so the win32 tray path uses the native .ico asset", () => {
+  assert.ok(existsSync(ICON_PNG_PATH), `expected ${ICON_PNG_PATH} to exist`);
+  assert.equal(
+    existsSync(ICON_ICO_PATH),
+    true,
+    "icon.ico is missing from bin/cli/tray/ — tray.ts::getIconPath() prefers it on win32 " +
+      "but silently falls back to icon.png when absent (bug #13535)"
+  );
+});
+
+test("bin/cli/tray/icon.png has a dark outline visible on both light and dark Windows tray backgrounds", async () => {
+  await assertHasVisibleContrastAgainstBothThemes(ICON_PNG_PATH, "bin/cli/tray/icon.png");
+});
+
+test("electron/assets/tray-icon.png has a dark outline visible on both light and dark tray backgrounds (Windows/Linux Electron tray, no template-image auto-tint)", async () => {
+  await assertHasVisibleContrastAgainstBothThemes(
+    ELECTRON_TRAY_ICON_PATH,
+    "electron/assets/tray-icon.png"
+  );
+});