diff --git a/packages/insomnia-inso/src/cli.ts b/packages/insomnia-inso/src/cli.ts
index fba4ca5555f..d596abbe95c 100644
--- a/packages/insomnia-inso/src/cli.ts
+++ b/packages/insomnia-inso/src/cli.ts
@@ -26,6 +26,7 @@ import { loadEnvironment, promptEnvironment } from './db/models/environment';
 import { loadTestSuites, promptTestSuites } from './db/models/unit-test-suite';
 import { matchIdIsh } from './db/models/util';
 import { loadWorkspace, promptWorkspace } from './db/models/workspace';
+import { generateDocumentation } from './scripts/docs';
 
 export interface GlobalOptions {
   ci: boolean;
@@ -711,5 +712,11 @@ Test results:`);
       program.parseAsync(scriptArgs).catch(logErrorAndExit);
     });
 
+  program.command('generate-docs')
+    .action(() => {
+      generateDocumentation(program);
+      return process.exit(1);
+    });
+
   program.parseAsync(args || process.argv).catch(logErrorAndExit);
 };
diff --git a/packages/insomnia-inso/src/scripts/docs.ts b/packages/insomnia-inso/src/scripts/docs.ts
new file mode 100644
index 00000000000..f47146f4342
--- /dev/null
+++ b/packages/insomnia-inso/src/scripts/docs.ts
@@ -0,0 +1,92 @@
+import path from 'node:path';
+
+import * as commander from 'commander';
+import fs from 'fs';
+
+import { version } from '../../package.json';
+
+const DOCS_DIR = path.join(__dirname, `../reference/insomnia-inso/${version}`);
+
+function writeMarkdownFile(fileName: string, content: string): void {
+    const outputPath = path.join(DOCS_DIR, fileName);
+    fs.writeFileSync(outputPath, content);
+}
+
+function generateOptionsMarkdown(options: readonly commander.Option[], title: string): string {
+    return options.length ? `## ${title}
+
+${options.map(option => `- \`${option.flags}\`: ${option.description}
+`).join('')}
+` : '';
+}
+
+function generateSubcommandsMarkdown(commandName: string, subcommands: { name: string; description: string }[]): string {
+    return subcommands.length ? `## Subcommands
+
+${subcommands.map(sub => `- [\`${commandName} ${sub.name}\`](/insomnia-inso/${commandName.replace(/\s+/g, '_')}_${sub.name.replace(/\s+/g, '_')}/): ${sub.description}
+`).join('')}
+` : '';
+}
+
+export function generateCommandMarkdown(command: commander.Command, programOptions: readonly commander.Option[], parentName?: string): { name: string; fileName: string; description: string; subcommands: readonly commander.Command[] } {
+    const commandName = parentName ? `${parentName} ${command.name()}` : command.name();
+    const fileName = `${commandName.replace(/\s+/g, '_')}.md`;
+
+    writeMarkdownFile(fileName, `# ${commandName}
+
+## Command Description
+
+${command.description()}
+
+## Syntax
+
+\`${commandName} ${command.usage() || '[options]'}\`
+
+${command.options.length > 0 ? generateOptionsMarkdown(command.options, 'Local Flags') : ''}${generateOptionsMarkdown(programOptions, 'Global Flags')}${generateSubcommandsMarkdown(commandName, command.commands.map(sub => ({
+    name: sub.name(),
+    description: sub.description() || 'No description available',
+})))}`);
+
+    return {
+        name: commandName,
+        fileName,
+        description: command.description() || 'No description available',
+        subcommands: command.commands,
+    };
+}
+
+export function generateDocumentation(program: commander.Command): void {
+    if (!fs.existsSync(DOCS_DIR)) {
+        fs.mkdirSync(DOCS_DIR, { recursive: true });
+    }
+
+    const allCommands: any[] = [];
+
+    program.commands.forEach(command => {
+        const commandData = generateCommandMarkdown(command, program.options, '');
+
+        allCommands.push({
+            name: commandData.name,
+            description: commandData.description,
+            fileName: commandData.fileName,
+            subcommands: commandData.subcommands.map(sub => ({
+                name: sub.name(),
+                description: sub.description() || 'No description available',
+                fileName: `${commandData.name.replace(/\s+/g, '_')}_${sub.name().replace(/\s+/g, '_')}.md`,
+            })),
+        });
+
+        commandData.subcommands.forEach(sub => {
+            generateCommandMarkdown(sub, program.options, commandData.name);
+        });
+    });
+
+    writeMarkdownFile('index.md', `# CLI Documentation 
+${generateOptionsMarkdown(program.options, 'Global Flags')}
+## Commands
+
+${allCommands.map(({ name, description, fileName }) => `- [\`${name}\`](/insomnia-inso/${fileName.replace('.md', '')}/): ${description}
+`).join('')}
+${allCommands.map(({ name, subcommands }) => `${generateSubcommandsMarkdown(name, subcommands)}
+`).join('')}`);
+}