diff --git a/CHANGELOG.md b/CHANGELOG.md
index f3ddf2ec03e..a0060e2e24e 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -41,6 +41,9 @@ Docs: https://docs.openclaw.ai
 - Auto-reply/TUI: keep fallback timeout recovery deliverable after a primary model lifecycle error by emitting fallback progress and deferring terminal TUI errors until recovery has a chance to finish. Fixes #80000. (#80009) Thanks @TurboTheTurtle.
 - CLI/agent: let `openclaw agent --model` use the backend/admin Gateway scope without cached device-token scopes silently downscoping the request. (#78837) Thanks @VACInc.
 - CLI/help: keep help and version invocations configless while improving shared port, channel, plugin, task, session, message, pairing, and auth recovery text.
+- CLI/config: explain strict JSON parse failures with a valid example and the plain-string escape hatch.
+- CLI/secrets: turn offline Gateway reload failures into actionable recovery text.
+- CLI/channels: explain missing or ambiguous channel selections with next commands.
 - Browser/Docker: detect Playwright-managed Chromium from `PLAYWRIGHT_BROWSERS_PATH` and the default Playwright cache on Linux, so Docker installs that persist `/home/node/.cache/ms-playwright` no longer need `browser.executablePath`.
 - Ollama: keep DeepSeek V4 cloud models thinking-capable even when Ollama Cloud `/api/show` omits the `thinking` capability, so `/think high` no longer rejects `ollama/deepseek-v4-*:cloud`.
 - ACPX/Claude ACP: keep foreground prompts waiting for their own result when autonomous task-notification results arrive during the same session, and retarget the patch for Claude Agent ACP `0.33.1`.
diff --git a/src/cli/config-cli.test.ts b/src/cli/config-cli.test.ts
index c0ddc248926..654b242d473 100644
--- a/src/cli/config-cli.test.ts
+++ b/src/cli/config-cli.test.ts
@@ -734,6 +734,12 @@ describe("config cli", () => {
 
       expect(mockWriteConfigFile).not.toHaveBeenCalled();
       expect(mockReadConfigFileSnapshot).not.toHaveBeenCalled();
+      expect(mockError).toHaveBeenCalledWith(
+        expect.stringContaining('Could not parse "{bad" as JSON for --strict-json.'),
+      );
+      expect(mockError).toHaveBeenCalledWith(
+        expect.stringContaining("For plain strings, omit --strict-json."),
+      );
     });
 
     it("keeps --json as a strict parsing alias", async () => {
diff --git a/src/cli/config-cli.ts b/src/cli/config-cli.ts
index 7267059c68f..2805fdc7557 100644
--- a/src/cli/config-cli.ts
+++ b/src/cli/config-cli.ts
@@ -60,6 +60,7 @@ import {
   type ConfigSetOptions,
 } from "./config-set-input.js";
 import { resolveConfigSetMode } from "./config-set-parser.js";
+import { formatStrictJsonParseFailure } from "./error-format.js";
 import { setCommandJsonMode } from "./program/json-mode.js";
 
 type PathSegment = string;
@@ -266,7 +267,7 @@ function parseValue(raw: string, opts: ConfigSetParseOpts): unknown {
     try {
       return JSON.parse(trimmed);
     } catch (err) {
-      throw new Error(`Failed to parse JSON value: ${String(err)}`, { cause: err });
+      throw new Error(formatStrictJsonParseFailure({ value: raw, cause: err }), { cause: err });
     }
   }
 
diff --git a/src/cli/error-format.ts b/src/cli/error-format.ts
index 5824888eff8..ae4b7b51bd5 100644
--- a/src/cli/error-format.ts
+++ b/src/cli/error-format.ts
@@ -48,6 +48,39 @@ export function formatUnsupportedChannelActionMessage(params: {
   )} to inspect supported actions.`;
 }
 
+export function formatStrictJsonParseFailure(params: { value: string; cause: unknown }): string {
+  const rawCause = params.cause instanceof Error ? params.cause.message : String(params.cause);
+  const cause = rawCause.trim().replace(/[.。]+$/u, "");
+  const preview =
+    params.value.length > 48 ? `${params.value.slice(0, 45).trimEnd()}...` : params.value;
+  return [
+    `Could not parse ${JSON.stringify(preview)} as JSON for --strict-json.`,
+    `${cause}.`,
+    `Use valid JSON, for example ${formatInlineCliCommand(
+      "openclaw config set gateway.port 18789 --strict-json",
+    )}.`,
+    "For plain strings, omit --strict-json.",
+  ].join(" ");
+}
+
+export function formatGatewayCommandFailure(params: {
+  action: string;
+  error: unknown;
+  inspectCommand?: string;
+}): string {
+  const raw = params.error instanceof Error ? params.error.message : String(params.error);
+  const message = raw
+    .replace(/\s*Run [`"]?openclaw doctor[`"]? for diagnostics\.?/gi, "")
+    .replace(/\s+/g, " ")
+    .trim()
+    .replace(/[.。]+$/u, "");
+  const inspectCommand = params.inspectCommand ?? "openclaw gateway status --deep";
+  const detail = message ? `: ${message}` : "";
+  return `Could not ${params.action} because the Gateway did not respond${detail}. Run ${formatInlineCliCommand(
+    inspectCommand,
+  )} to inspect the active Gateway.`;
+}
+
 export function formatLookupMiss(params: {
   noun: string;
   value: string;
diff --git a/src/cli/secrets-cli.test.ts b/src/cli/secrets-cli.test.ts
index 70db46b554a..456b6a51362 100644
--- a/src/cli/secrets-cli.test.ts
+++ b/src/cli/secrets-cli.test.ts
@@ -175,6 +175,22 @@ describe("secrets CLI", () => {
     expect(runtimeLogs.at(-1)).toContain('"ok": true');
   });
 
+  it("explains Gateway reload failures without duplicate doctor noise", async () => {
+    callGatewayFromCli.mockRejectedValue(
+      new Error("gateway closed (1006 abnormal closure). Run `openclaw doctor` for diagnostics."),
+    );
+
+    await expect(
+      createProgram().parseAsync(["secrets", "reload"], { from: "user" }),
+    ).rejects.toThrow("__exit__:1");
+
+    expect(runtimeErrors.at(-1)).toContain(
+      "Could not reload secrets because the Gateway did not respond: gateway closed (1006 abnormal closure).",
+    );
+    expect(runtimeErrors.at(-1)).toContain("openclaw gateway status --deep");
+    expect(runtimeErrors.at(-1)).not.toContain("diagnostics..");
+  });
+
   it("runs secrets audit and exits via check code", async () => {
     runSecretsAudit.mockResolvedValue({
       version: 1,
diff --git a/src/cli/secrets-cli.ts b/src/cli/secrets-cli.ts
index 7b6616aa2f1..4baefe8b926 100644
--- a/src/cli/secrets-cli.ts
+++ b/src/cli/secrets-cli.ts
@@ -11,6 +11,7 @@ import { isSecretsApplyPlan, type SecretsApplyPlan } from "../secrets/plan.js";
 import { formatDocsLink } from "../terminal/links.js";
 import { theme } from "../terminal/theme.js";
 import { formatCliCommand } from "./command-format.js";
+import { formatGatewayCommandFailure } from "./error-format.js";
 import { addGatewayClientOptions, callGatewayFromCli, type GatewayRpcOpts } from "./gateway-rpc.js";
 
 type SecretsReloadOptions = GatewayRpcOpts & { json?: boolean };
@@ -82,7 +83,11 @@ export function registerSecretsCli(program: Command) {
     } catch (err) {
       defaultRuntime.error(
         danger(
-          `Secrets reload failed: ${formatErrorMessage(err)}. Run ${formatCliCommand("openclaw gateway status --deep")} to inspect the active gateway.`,
+          formatGatewayCommandFailure({
+            action: "reload secrets",
+            error: err,
+            inspectCommand: "openclaw gateway status --deep",
+          }),
         ),
       );
       defaultRuntime.exit(1);
diff --git a/src/infra/outbound/channel-selection.test.ts b/src/infra/outbound/channel-selection.test.ts
index e83c48bd930..d2a3ef7cbfa 100644
--- a/src/infra/outbound/channel-selection.test.ts
+++ b/src/infra/outbound/channel-selection.test.ts
@@ -271,7 +271,8 @@ describe("resolveMessageChannelSelection", () => {
     },
     {
       params: { cfg: {} as never },
-      expectedMessage: "Channel is required (no configured channels detected).",
+      expectedMessage:
+        "Channel is required (no configured channels detected). Run openclaw channels add to configure one",
     },
     {
       setup: () => {
@@ -292,7 +293,8 @@ describe("resolveMessageChannelSelection", () => {
         ]);
       },
       params: { cfg: { channels: { whatsapp: { enabled: true } } } as never },
-      expectedMessage: "Channel is required (no configured channels detected).",
+      expectedMessage:
+        "Channel is required (no configured channels detected). Run openclaw channels add to configure one",
     },
     {
       setup: () => {
@@ -302,7 +304,8 @@ describe("resolveMessageChannelSelection", () => {
         ]);
       },
       params: { cfg: {} as never },
-      expectedMessage: "Channel is required when multiple channels are configured: beta, gamma",
+      expectedMessage:
+        "Channel is required when multiple channels are configured: beta, gamma. Pass --channel <channel> to choose one.",
     },
   ])("rejects invalid channel selection for %j", async ({ setup, params, expectedMessage }) => {
     setup?.();
diff --git a/src/infra/outbound/channel-selection.ts b/src/infra/outbound/channel-selection.ts
index a6c3b132699..a7414703339 100644
--- a/src/infra/outbound/channel-selection.ts
+++ b/src/infra/outbound/channel-selection.ts
@@ -102,6 +102,21 @@ function formatMissingOfficialExternalChannelsMessage(
   return `Configured official external channels ${labels} are missing their plugins. Run: openclaw doctor --fix, or install individually: ${installCommands}.`;
 }
 
+function formatNoConfiguredChannelsMessage(): string {
+  return [
+    "Channel is required (no configured channels detected).",
+    "Run openclaw channels add to configure one, or pass --channel <channel> after enabling a channel.",
+    "Use openclaw channels list --all to see available channel ids.",
+  ].join(" ");
+}
+
+function formatMultipleConfiguredChannelsMessage(configured: readonly string[]): string {
+  return [
+    `Channel is required when multiple channels are configured: ${configured.join(", ")}.`,
+    "Pass --channel <channel> to choose one.",
+  ].join(" ");
+}
+
 function isAccountEnabled(account: unknown): boolean {
   if (!account || typeof account !== "object") {
     return true;
@@ -263,11 +278,9 @@ export async function resolveMessageChannelSelection(params: {
         `Channel is required (no available channels detected). ${formatMissingOfficialExternalChannelsMessage(repairHints)}`,
       );
     }
-    throw new Error("Channel is required (no configured channels detected).");
+    throw new Error(formatNoConfiguredChannelsMessage());
   }
-  throw new Error(
-    `Channel is required when multiple channels are configured: ${configured.join(", ")}`,
-  );
+  throw new Error(formatMultipleConfiguredChannelsMessage(configured));
 }
 
 export const __testing = {