diff --git a/docs/docs/features/argument-parsing/examples/boolean-flag.txt b/docs/docs/features/argument-parsing/examples/boolean-flag.txt
index dce4623..8947bd2 100644
--- a/docs/docs/features/argument-parsing/examples/boolean-flag.txt
+++ b/docs/docs/features/argument-parsing/examples/boolean-flag.txt
@@ -19,9 +19,9 @@ export const root = buildCommand({
   docs: {
     brief: "Example for live playground with boolean flag",
     customUsage: [
-      "--quiet",
-      "--quiet=yes",
-      "--noQuiet",
+      { input: "--quiet", brief: "Flag with no value" },
+      { input: "--quiet=yes", brief: "Flag with explicit value" },
+      { input: "--noQuiet", brief: "Negated flag" },
     ],
   },
 });
diff --git a/docs/docs/features/command-routing/commands.mdx b/docs/docs/features/command-routing/commands.mdx
index 50af806..c9d07b3 100644
--- a/docs/docs/features/command-routing/commands.mdx
+++ b/docs/docs/features/command-routing/commands.mdx
@@ -68,7 +68,7 @@ The parameters object is a specification of all of the parameters (arguments and
 
 A base level of documentation is required, and more is always appreciated. All commands must specify a value for `brief` that contains a short line of text to be used when referring to this command throughout the help text of the application.
 
-Optionally, you can further customize the help text for this specific command by including `fullDescription` or `customUsage`. The former will override `brief` in the command's help text and can contain multiple lines of text rather than just one. The `customUsage` property will replace the auto-generated usage lines, and is useful when there's some [additional validation of user inputs](../out-of-scope.mdx#cross-argument-validation) that isn't represented natively by Stricli.
+Optionally, you can further customize the help text for this specific command by including `fullDescription` or `customUsage`. The former will override `brief` in the command's help text and can contain multiple lines of text rather than just one. The `customUsage` property will replace the auto-generated usage lines, and is useful when there's some [additional validation of user inputs](../out-of-scope.mdx#cross-argument-validation) that isn't represented natively by Stricli. You can also provide an object with `input` and `brief` to print a description after the usage line.
 
 ```ts
 // output-next-line
@@ -84,6 +84,7 @@ buildCommand({
     customUsage: [
       "-a -b",
       "-c",
+      { input: "-d", brief: "Brief description of this use case" },
     ],
   },
   ...
@@ -98,6 +99,8 @@ run --help
 USAGE
   run -a -b
   run -c
+  run -d
+    Brief description of this use case
   run --help
 
 This is the full description of the command.
diff --git a/packages/core/src/routing/command/documentation.ts b/packages/core/src/routing/command/documentation.ts
index bae4c64..14428f0 100644
--- a/packages/core/src/routing/command/documentation.ts
+++ b/packages/core/src/routing/command/documentation.ts
@@ -6,6 +6,11 @@ import { formatDocumentationForPositionalParameters } from "../../parameter/posi
 import type { CommandParameters } from "../../parameter/types";
 import type { HelpFormattingArguments } from "../types";
 
+export interface CustomUsage {
+    readonly input: string;
+    readonly brief: string;
+}
+
 export interface CommandDocumentation {
     /**
      * In-line documentation for this command.
@@ -18,7 +23,7 @@ export interface CommandDocumentation {
     /**
      * Sample usage to replace the generated usage lines.
      */
-    readonly customUsage?: readonly string[];
+    readonly customUsage?: readonly (string | CustomUsage)[];
 }
 
 /**
@@ -34,8 +39,13 @@ export function* generateCommandHelpLines(
     const prefix = args.prefix.join(" ");
     yield args.ansiColor ? `\x1B[1m${headers.usage}\x1B[22m` : headers.usage;
     if (customUsage) {
-        for (const customUsageLine of customUsage) {
-            yield `  ${prefix} ${customUsageLine}`;
+        for (const usage of customUsage) {
+            if (typeof usage === "string") {
+                yield `  ${prefix} ${usage}`;
+            } else {
+                const brief = args.ansiColor ? `\x1B[3m${usage.brief}\x1B[23m` : usage.brief;
+                yield `  ${prefix} ${usage.input}\n    ${brief}`;
+            }
         }
     } else {
         yield `  ${formatUsageLineForParameters(parameters, args)}`;
diff --git a/packages/core/tests/application.spec.ts b/packages/core/tests/application.spec.ts
index 7c7696a..398728d 100644
--- a/packages/core/tests/application.spec.ts
+++ b/packages/core/tests/application.spec.ts
@@ -674,7 +674,11 @@ describe("Application", () => {
                     },
                     docs: {
                         brief: "basic command",
-                        customUsage: ["custom usage 1", "custom usage 2", "custom usage 3"],
+                        customUsage: [
+                            "custom usage 1",
+                            { input: "custom-two", brief: "enhanced custom usage 2" },
+                            "custom usage 3",
+                        ],
                     },
                 });
                 const appWithAlternateUsage = buildApplication(commandWithAlternateUsage, {
@@ -1526,6 +1530,65 @@ describe("Application", () => {
                 compareToBaseline(this, ApplicationRunResultBaselineFormat, result);
             });
         });
+
+        describe("nested basic route map with hidden routes, always show help-all (alias)", () => {
+            // GIVEN
+            const rootRouteMap = buildRouteMapForFakeContext({
+                routes: {
+                    sub: buildBasicRouteMap("sub"),
+                    subHidden: buildBasicRouteMap("subHidden"),
+                },
+                docs: {
+                    brief: "root route map",
+                    hideRoute: {
+                        subHidden: true,
+                    },
+                },
+            });
+            const app = buildApplication(rootRouteMap, {
+                name: "cli",
+                documentation: {
+                    alwaysShowHelpAllFlag: true,
+                    useAliasInUsageLine: true,
+                },
+            });
+
+            // WHEN
+            it("display help text for root (implicit)", async function () {
+                const result = await runWithInputs(app, []);
+                compareToBaseline(this, ApplicationRunResultBaselineFormat, result);
+            });
+
+            it("display help text for root", async function () {
+                const result = await runWithInputs(app, ["--help"]);
+                compareToBaseline(this, ApplicationRunResultBaselineFormat, result);
+            });
+
+            it("display help text for root including hidden", async function () {
+                const result = await runWithInputs(app, ["--help-all"]);
+                compareToBaseline(this, ApplicationRunResultBaselineFormat, result);
+            });
+
+            it("fails for undefined route", async function () {
+                const result = await runWithInputs(app, ["undefined"]);
+                compareToBaseline(this, ApplicationRunResultBaselineFormat, result);
+            });
+
+            it("fails for undefined flag", async function () {
+                const result = await runWithInputs(app, ["--undefined"]);
+                compareToBaseline(this, ApplicationRunResultBaselineFormat, result);
+            });
+
+            it("displays help text for nested hidden route map (implicit)", async function () {
+                const result = await runWithInputs(app, ["subHidden"]);
+                compareToBaseline(this, ApplicationRunResultBaselineFormat, result);
+            });
+
+            it("displays help text for nested hidden route map", async function () {
+                const result = await runWithInputs(app, ["subHidden", "--help"]);
+                compareToBaseline(this, ApplicationRunResultBaselineFormat, result);
+            });
+        });
     });
 
     describe("proposeCompletions", () => {
diff --git a/packages/core/tests/baselines/reference/application.txt b/packages/core/tests/baselines/reference/application.txt
index 1495914..d6334ac 100644
--- a/packages/core/tests/baselines/reference/application.txt
+++ b/packages/core/tests/baselines/reference/application.txt
@@ -245,7 +245,8 @@ ExitCode=Success
 :: STDOUT
 USAGE
   cli custom usage 1
-  cli custom usage 2
+  cli custom-two
+    enhanced custom usage 2
   cli custom usage 3
   cli --help
 
@@ -1085,6 +1086,117 @@ ExitCode=UnknownCommand
 :: STDERR
 No command registered for `undefined`
 
+:::: Application / run / nested basic route map with hidden routes, always show help-all (alias) / display help text for root
+ExitCode=Success
+:: STDOUT
+USAGE
+  cli sub command ...
+  cli -h
+  cli -H
+
+root route map
+
+FLAGS
+  -h --help     Print help information and exit
+  -H --helpAll  Print help information (including hidden commands/flags) and exit
+
+COMMANDS
+  sub  sub
+
+:: STDERR
+
+:::: Application / run / nested basic route map with hidden routes, always show help-all (alias) / display help text for root (implicit)
+ExitCode=Success
+:: STDOUT
+USAGE
+  cli sub command ...
+  cli -h
+  cli -H
+
+root route map
+
+FLAGS
+  -h --help     Print help information and exit
+  -H --helpAll  Print help information (including hidden commands/flags) and exit
+
+COMMANDS
+  sub  sub
+
+:: STDERR
+
+:::: Application / run / nested basic route map with hidden routes, always show help-all (alias) / display help text for root including hidden
+ExitCode=Success
+:: STDOUT
+USAGE
+  cli sub command ...
+  cli subHidden command ...
+  cli -h
+  cli -H
+
+root route map
+
+FLAGS
+  -h --help     Print help information and exit
+  -H --helpAll  Print help information (including hidden commands/flags) and exit
+
+COMMANDS
+  sub        sub
+  subHidden  subHidden
+
+:: STDERR
+
+:::: Application / run / nested basic route map with hidden routes, always show help-all (alias) / displays help text for nested hidden route map
+ExitCode=Success
+:: STDOUT
+USAGE
+  cli subHidden command
+  cli subHidden -h
+  cli subHidden -H
+
+subHidden
+
+FLAGS
+  -h --help     Print help information and exit
+  -H --helpAll  Print help information (including hidden commands/flags) and exit
+
+COMMANDS
+  command  basic command
+
+:: STDERR
+
+:::: Application / run / nested basic route map with hidden routes, always show help-all (alias) / displays help text for nested hidden route map (implicit)
+ExitCode=Success
+:: STDOUT
+USAGE
+  cli subHidden command
+  cli subHidden -h
+  cli subHidden -H
+
+subHidden
+
+FLAGS
+  -h --help     Print help information and exit
+  -H --helpAll  Print help information (including hidden commands/flags) and exit
+
+COMMANDS
+  command  basic command
+
+:: STDERR
+
+:::: Application / run / nested basic route map with hidden routes, always show help-all (alias) / fails for undefined flag
+ExitCode=UnknownCommand
+:: STDOUT
+
+:: STDERR
+No command registered for `--undefined`
+
+:::: Application / run / nested basic route map with hidden routes, always show help-all (alias) / fails for undefined route
+ExitCode=UnknownCommand
+:: STDOUT
+
+:: STDERR
+No command registered for `undefined`
+
 :::: Application / run / nested basic route map with hidden routes, always show help-all / display help text for root
 ExitCode=Success
 :: STDOUT
diff --git a/packages/core/tests/baselines/reference/routing/command.txt b/packages/core/tests/baselines/reference/routing/command.txt
index 8c1f307..7567ba3 100644
--- a/packages/core/tests/baselines/reference/routing/command.txt
+++ b/packages/core/tests/baselines/reference/routing/command.txt
@@ -256,6 +256,26 @@ USAGE
 
 brief
 
+FLAGS
+  -a  --alpha            alpha flag brief
+      --bravo...         bravo flag brief
+     [--charlie]         charlie flag brief
+  -d  --delta/--noDelta  delta flag brief
+  -h  --help             Print help information and exit
+
+ARGUMENTS
+  args...  string array brief
+
+:::: Command / printHelp / mixed parameters, enhanced custom usage
+USAGE
+  prefix -a 1
+    enhanced usage line #1
+  prefix -a 2 -d
+    enhanced usage line #2
+  prefix --help
+
+brief
+
 FLAGS
   -a  --alpha            alpha flag brief
       --bravo...         bravo flag brief
@@ -307,6 +327,49 @@ USAGE
 
 Longer description of this command's behavior, only printed during --help
 
+FLAGS
+  -a  --alpha            alpha flag brief
+      --bravo...         bravo flag brief
+     [--charlie]         charlie flag brief
+  -d  --delta/--noDelta  delta flag brief
+  -h  --help             Print help information and exit
+
+ARGUMENTS
+  args...  string array brief
+
+:::: Command / printHelp / mixed parameters, help all, force alias in usage line
+USAGE
+  prefix (-a value) (--bravo value)... [--charlie c] (-d) <args>...
+  prefix -h
+  prefix -H
+
+brief
+
+FLAGS
+  -a  --alpha            alpha flag brief
+      --bravo...         bravo flag brief
+     [--charlie]         charlie flag brief
+  -d  --delta/--noDelta  delta flag brief
+  -h  --help             Print help information and exit
+  -H  --helpAll          Print help information (including hidden commands/flags) and exit
+
+ARGUMENTS
+  args...  string array brief
+
+:::: Command / printHelp / mixed parameters, mixed custom usage
+USAGE
+  prefix -a 1
+    enhanced usage line #1
+  prefix normal custom usage A
+  prefix normal custom usage B
+  prefix -a 2 -d
+    enhanced usage line #2
+  prefix normal custom usage C
+  prefix normal custom usage D
+  prefix --help
+
+brief
+
 FLAGS
   -a  --alpha            alpha flag brief
       --bravo...         bravo flag brief
@@ -442,6 +505,18 @@ brief
 FLAGS
   -h --help  Print help information and exit
 
+:::: Command / printHelp / no parameters, help all, force alias in usage line
+USAGE
+  prefix
+  prefix -h
+  prefix -H
+
+brief
+
+FLAGS
+  -h --help     Print help information and exit
+  -H --helpAll  Print help information (including hidden commands/flags) and exit
+
 :::: Command / run / command function returns error / with custom exit code
 ExitCode=Unknown(10)
 :: STDOUT
diff --git a/packages/core/tests/routing/command.spec.ts b/packages/core/tests/routing/command.spec.ts
index 121a598..ae9f740 100644
--- a/packages/core/tests/routing/command.spec.ts
+++ b/packages/core/tests/routing/command.spec.ts
@@ -330,6 +330,32 @@ describe("Command", function () {
             compareToBaseline(this, StringArrayBaselineFormat, helpString.split("\n"));
         });
 
+        it("no parameters, help all, force alias in usage line", function () {
+            // GIVEN
+            const command = buildCommand({
+                loader: async () => {
+                    return {
+                        default: (flags: {}) => {},
+                    };
+                },
+                parameters: {},
+                docs: { brief: "brief" },
+            });
+
+            // WHEN
+            const helpString = command.formatHelp({
+                ...defaultArgs,
+                includeHelpAllFlag: true,
+                config: {
+                    ...defaultArgs.config,
+                    useAliasInUsageLine: true,
+                },
+            });
+
+            // THEN
+            compareToBaseline(this, StringArrayBaselineFormat, helpString.split("\n"));
+        });
+
         it("mixed parameters", function () {
             // GIVEN
             const command = buildCommand({
@@ -1201,6 +1227,150 @@ describe("Command", function () {
             compareToBaseline(this, StringArrayBaselineFormat, helpString.split("\n"));
         });
 
+        it("mixed parameters, enhanced custom usage", function () {
+            // GIVEN
+            const command = buildCommand({
+                loader: async () => {
+                    return {
+                        default: (
+                            flags: { alpha: number; bravo: number[]; charlie?: number; delta: boolean },
+                            ...args: string[]
+                        ) => {},
+                    };
+                },
+                parameters: {
+                    positional: {
+                        kind: "array",
+                        parameter: {
+                            brief: "string array brief",
+                            parse: (x) => x,
+                        },
+                    },
+                    flags: {
+                        alpha: {
+                            brief: "alpha flag brief",
+                            kind: "parsed",
+                            parse: numberParser,
+                        },
+                        bravo: {
+                            brief: "bravo flag brief",
+                            kind: "parsed",
+                            variadic: true,
+                            parse: numberParser,
+                        },
+                        charlie: {
+                            brief: "charlie flag brief",
+                            placeholder: "c",
+                            kind: "parsed",
+                            optional: true,
+                            parse: numberParser,
+                        },
+                        delta: {
+                            brief: "delta flag brief",
+                            kind: "boolean",
+                        },
+                    },
+                    aliases: {
+                        a: "alpha",
+                        d: "delta",
+                    },
+                },
+                docs: {
+                    brief: "brief",
+                    customUsage: [
+                        {
+                            input: "-a 1",
+                            brief: "enhanced usage line #1",
+                        },
+                        {
+                            input: "-a 2 -d",
+                            brief: "enhanced usage line #2",
+                        },
+                    ],
+                },
+            });
+
+            // WHEN
+            const helpString = command.formatHelp(defaultArgs);
+
+            // THEN
+            compareToBaseline(this, StringArrayBaselineFormat, helpString.split("\n"));
+        });
+
+        it("mixed parameters, mixed custom usage", function () {
+            // GIVEN
+            const command = buildCommand({
+                loader: async () => {
+                    return {
+                        default: (
+                            flags: { alpha: number; bravo: number[]; charlie?: number; delta: boolean },
+                            ...args: string[]
+                        ) => {},
+                    };
+                },
+                parameters: {
+                    positional: {
+                        kind: "array",
+                        parameter: {
+                            brief: "string array brief",
+                            parse: (x) => x,
+                        },
+                    },
+                    flags: {
+                        alpha: {
+                            brief: "alpha flag brief",
+                            kind: "parsed",
+                            parse: numberParser,
+                        },
+                        bravo: {
+                            brief: "bravo flag brief",
+                            kind: "parsed",
+                            variadic: true,
+                            parse: numberParser,
+                        },
+                        charlie: {
+                            brief: "charlie flag brief",
+                            placeholder: "c",
+                            kind: "parsed",
+                            optional: true,
+                            parse: numberParser,
+                        },
+                        delta: {
+                            brief: "delta flag brief",
+                            kind: "boolean",
+                        },
+                    },
+                    aliases: {
+                        a: "alpha",
+                        d: "delta",
+                    },
+                },
+                docs: {
+                    brief: "brief",
+                    customUsage: [
+                        {
+                            input: "-a 1",
+                            brief: "enhanced usage line #1",
+                        },
+                        "normal custom usage A",
+                        "normal custom usage B",
+                        {
+                            input: "-a 2 -d",
+                            brief: "enhanced usage line #2",
+                        },
+                        "normal custom usage C",
+                        "normal custom usage D",
+                    ],
+                },
+            });
+
+            // WHEN
+            const helpString = command.formatHelp(defaultArgs);
+
+            // THEN
+            compareToBaseline(this, StringArrayBaselineFormat, helpString.split("\n"));
+        });
+
         it("mixed parameters with `original` display case style", function () {
             // GIVEN
             const command = buildCommand({
@@ -1776,6 +1946,73 @@ describe("Command", function () {
             // THEN
             compareToBaseline(this, StringArrayBaselineFormat, helpString.split("\n"));
         });
+
+        it("mixed parameters, help all, force alias in usage line", function () {
+            // GIVEN
+            const command = buildCommand({
+                loader: async () => {
+                    return {
+                        default: (
+                            flags: { alpha: number; bravo: number[]; charlie?: number; delta: boolean },
+                            ...args: string[]
+                        ) => {},
+                    };
+                },
+                parameters: {
+                    positional: {
+                        kind: "array",
+                        parameter: {
+                            brief: "string array brief",
+                            parse: (x) => x,
+                        },
+                    },
+                    flags: {
+                        alpha: {
+                            brief: "alpha flag brief",
+                            kind: "parsed",
+                            parse: numberParser,
+                        },
+                        bravo: {
+                            brief: "bravo flag brief",
+                            kind: "parsed",
+                            variadic: true,
+                            parse: numberParser,
+                        },
+                        charlie: {
+                            brief: "charlie flag brief",
+                            placeholder: "c",
+                            kind: "parsed",
+                            optional: true,
+                            parse: numberParser,
+                        },
+                        delta: {
+                            brief: "delta flag brief",
+                            kind: "boolean",
+                        },
+                    },
+                    aliases: {
+                        a: "alpha",
+                        d: "delta",
+                    },
+                },
+                docs: {
+                    brief: "brief",
+                },
+            });
+
+            // WHEN
+            const helpString = command.formatHelp({
+                ...defaultArgs,
+                includeHelpAllFlag: true,
+                config: {
+                    ...defaultArgs.config,
+                    useAliasInUsageLine: true,
+                },
+            });
+
+            // THEN
+            compareToBaseline(this, StringArrayBaselineFormat, helpString.split("\n"));
+        });
     });
 
     describe("run", function () {