diff --git a/apps/yaak-proxy/components/AppIcon.tsx b/apps/yaak-proxy/components/AppIcon.tsx
index c90b0a824..74f9b12e9 100644
--- a/apps/yaak-proxy/components/AppIcon.tsx
+++ b/apps/yaak-proxy/components/AppIcon.tsx
@@ -42,8 +42,13 @@ export function AppIcon({ path, className = "size-4" }: { path: string; classNam
   }, [path]);
 
   return url == null ? (
-    <span aria-hidden className={classNames(className, "inline-block shrink-0")} />
+    <span aria-hidden className={classNames(className, "inline-block shrink-0 aspect-square")} />
   ) : (
-    <img alt="" src={url} className={classNames(className, "shrink-0")} />
+    // Square whatever squeezes it, beside text that truncates
+    <img
+      alt=""
+      src={url}
+      className={classNames(className, "shrink-0 aspect-square object-contain")}
+    />
   );
 }
diff --git a/apps/yaak-proxy/components/EncryptedCard.tsx b/apps/yaak-proxy/components/EncryptedCard.tsx
index 96db399d3..ec64cfab3 100644
--- a/apps/yaak-proxy/components/EncryptedCard.tsx
+++ b/apps/yaak-proxy/components/EncryptedCard.tsx
@@ -185,6 +185,11 @@ function LineText({ line }: { line: Line }) {
         typeof part === "string" ? (
           // oxlint-disable-next-line react/no-array-index-key -- the parts of one fixed line
           <span key={i}>{part}</span>
+        ) : "bold" in part ? (
+          // oxlint-disable-next-line react/no-array-index-key -- the parts of one fixed line
+          <span key={i} className="font-semibold">
+            {part.bold}
+          </span>
         ) : (
           // oxlint-disable-next-line react/no-array-index-key -- the parts of one fixed line
           <InlineCode key={i}>{part.code}</InlineCode>
@@ -222,7 +227,7 @@ function ActionButton({
       flow.clientPath == null ? (
         <Icon icon="box" size="sm" />
       ) : (
-        <AppIcon path={flow.clientPath} className="size-4" />
+        <AppIcon path={flow.clientPath} className="size-4 min-w-4" />
       )
     ) : (
       <Icon icon={ICONS[action.icon]} size="sm" />
@@ -241,7 +246,7 @@ function ActionButton({
         action.hint == null ? undefined : (
           <span
             className={classNames(
-              "ml-auto pl-3 font-mono text-xs text-text-subtlest truncate max-w-[50%]",
+              "block ml-auto pl-3 font-mono text-xs text-text-subtlest truncate max-w-[11rem]",
               action.removes && "line-through",
             )}
           >
diff --git a/apps/yaak-proxy/components/HttpsStrip.tsx b/apps/yaak-proxy/components/HttpsStrip.tsx
index 632aa594e..8bbc5a399 100644
--- a/apps/yaak-proxy/components/HttpsStrip.tsx
+++ b/apps/yaak-proxy/components/HttpsStrip.tsx
@@ -77,9 +77,9 @@ export function HttpsStrip() {
         app.path == null ? (
           app.name
         ) : (
-          <span className="flex items-center gap-2">
-            <AppIcon path={app.path} className="size-4" />
-            {app.name}
+          <span className="flex items-center gap-2 min-w-0">
+            <AppIcon path={app.path} className="size-4 min-w-4" />
+            <span className="truncate">{app.name}</span>
           </span>
         ),
       keepOpenOnSelect: true,
diff --git a/apps/yaak-proxy/components/Sidebar.tsx b/apps/yaak-proxy/components/Sidebar.tsx
index 1d5f6d8b5..434a50833 100644
--- a/apps/yaak-proxy/components/Sidebar.tsx
+++ b/apps/yaak-proxy/components/Sidebar.tsx
@@ -85,7 +85,9 @@ function ItemInner({ item }: { item: SidebarItem }) {
       {item.kind === "encrypted" && <Icon icon="lock" size="sm" className="text-text-subtle" />}
       {item.kind === "saved" && <Icon icon="bookmark" size="sm" className="text-text-subtle" />}
       {item.kind === "folder" && <Icon icon="folder" size="sm" className="text-text-subtle" />}
-      {item.appPath != null && <AppIcon path={item.appPath} className="size-[1.125rem]" />}
+      {item.appPath != null && (
+        <AppIcon path={item.appPath} className="size-[1.125rem] min-w-[1.125rem]" />
+      )}
       {item.kind === "folder" && item.path != null ? (
         // Named by its last part; the whole path on hover
         <Tooltip wrap content={item.path} delay={CONTROL_TOOLTIP_DELAY}>
diff --git a/apps/yaak-proxy/harness/httpsFixtures.ts b/apps/yaak-proxy/harness/httpsFixtures.ts
index 4fa7a659c..765165470 100644
--- a/apps/yaak-proxy/harness/httpsFixtures.ts
+++ b/apps/yaak-proxy/harness/httpsFixtures.ts
@@ -40,6 +40,12 @@ const apps = {
     clientBundleId: "com.1password.1password",
     clientPath: "/Applications/1Password.app",
   },
+  headless: {
+    clientName: "chrome-headless-shell",
+    clientBundleId: null,
+    clientPath:
+      "/Users/you/.cache/ms-playwright/chromium_headless_shell-1208/chrome-headless-shell",
+  },
   acme: {
     clientName: "Acme Sync",
     clientBundleId: "dev.acme.sync",
@@ -124,6 +130,7 @@ function encryptedScene(): Flow[] {
     tunnel(10, "fonts.gstatic.com", apps.dia),
     tunnel(11, "clients2.google.com", apps.chrome),
     tunnel(12, "home.taila714c.ts.net:8317", apps.dia, { url: "home.taila714c.ts.net:8317" }),
+    tunnel(13, "optimizationguide-pa.googleapis.com", apps.headless),
   ];
 }
 
diff --git a/apps/yaak-proxy/lib/encryptedCard.test.ts b/apps/yaak-proxy/lib/encryptedCard.test.ts
index 69ea1f72a..c8ab5062d 100644
--- a/apps/yaak-proxy/lib/encryptedCard.test.ts
+++ b/apps/yaak-proxy/lib/encryptedCard.test.ts
@@ -90,7 +90,9 @@ describe("the card of an encrypted connection", () => {
 
   test("something else listed: not on the list, with the same choices", () => {
     const c = card({ list: [...user("host:api.stripe.com"), ...BUILT_INS] });
-    expect(lineText(c.why)).toBe("Decryption not configured for `www.google.com`");
+    expect(lineText(c.why)).toBe(
+      "**Encrypted Content:** Enable decryption to see requests to `www.google.com`",
+    );
     expect(c.actions.map((a) => a.label)).toEqual([
       "Decrypt www.google.com",
       "Decrypt Dia",
@@ -108,10 +110,10 @@ describe("the card of an encrypted connection", () => {
   test("names the host nothing on the list covers, its port only when not 443", () => {
     const list = [...user("host:api.stripe.com"), ...BUILT_INS];
     expect(lineText(card({ list, flow: { ...tunnel, url: "t.yaak.app:443" } }).why)).toBe(
-      "Decryption not configured for `t.yaak.app`",
+      "**Encrypted Content:** Enable decryption to see requests to `t.yaak.app`",
     );
     expect(lineText(card({ list, flow: { ...tunnel, url: "home.ts.net:8317" } }).why)).toBe(
-      "Decryption not configured for `home.ts.net:8317`",
+      "**Encrypted Content:** Enable decryption to see requests to `home.ts.net:8317`",
     );
   });
 
diff --git a/apps/yaak-proxy/lib/encryptedCard.ts b/apps/yaak-proxy/lib/encryptedCard.ts
index dd3027a9d..3c86cc648 100644
--- a/apps/yaak-proxy/lib/encryptedCard.ts
+++ b/apps/yaak-proxy/lib/encryptedCard.ts
@@ -78,12 +78,19 @@ export interface CardAction {
   icon: "host" | "app" | "everything" | "lock" | "lock_open" | "refresh" | "shield" | "terminal";
 }
 
-/** A line of text, the hosts, apps and entries in it shown as code, as Yaak shows literal values */
-export type Line = (string | { code: string })[];
+/**
+ * A line of text, the hosts, apps and entries in it shown as code, as Yaak shows literal values,
+ * and a lead in bold
+ */
+export type Line = (string | { code: string } | { bold: string })[];
 
-/** A line as plain text, its code in backticks */
+/** A line as plain text, its code in backticks and its bold in asterisks */
 export function lineText(line: Line): string {
-  return line.map((part) => (typeof part === "string" ? part : `\`${part.code}\``)).join("");
+  return line
+    .map((part) =>
+      typeof part === "string" ? part : "code" in part ? `\`${part.code}\`` : `**${part.bold}**`,
+    )
+    .join("");
 }
 
 export interface EncryptedCardModel {
@@ -265,7 +272,11 @@ function whyLine(
       ? ["Nothing is decrypted yet"]
       : decryptsNow
         ? ["Not on the decrypt list"]
-        : ["Decryption not configured for ", { code: c.label }],
+        : [
+            { bold: "Encrypted Content:" },
+            " Enable decryption to see requests to ",
+            { code: c.label },
+          ],
     whySub: null,
   };
 }