diff --git a/bin/run b/bin/run
index b77a780b..0ad89bc1 100755
--- a/bin/run
+++ b/bin/run
@@ -1,8 +1,5 @@
 #!/usr/bin/env node
 
-/* tslint:disable:no-var-requires only-arrow-functions */
-/* eslint-disable global-require, prefer-arrow-callback */
-
 // Since the CLI is a single process, we can have a larger amount of max listeners since
 // the process gets shut down. Don't set it to 0 (no limit) since we should still be aware
 // of rouge event listeners
@@ -14,6 +11,9 @@ process.setMaxListeners = () => {};
 // Check node version before requiring additional packages
 require('../dist/versions').checkNodeVersion();
 
+// Pre-process/prune flags before creating or running the actual CLI
+require('../dist/flags').preprocessCliFlags(process);
+
 const cli = require('../dist/cli');
 const pjson = require('../package.json');
 
diff --git a/src/flags.ts b/src/flags.ts
new file mode 100644
index 00000000..79fe64ad
--- /dev/null
+++ b/src/flags.ts
@@ -0,0 +1,43 @@
+/*
+ * Copyright (c) 2020, salesforce.com, inc.
+ * All rights reserved.
+ * Licensed under the BSD 3-Clause license.
+ * For full license text, see LICENSE.txt file in the repo root or https://opensource.org/licenses/BSD-3-Clause
+ */
+
+// -------------------------------------------------------------------------------
+// No requires or imports since this is loaded early in the cli lifecycle and we
+// want to minimize the number of packages that load before enabling require
+// instrumentation.
+// -------------------------------------------------------------------------------
+
+export interface ProcessLike {
+  argv: string[];
+  env: { [key: string]: string | undefined };
+}
+
+export function preprocessCliFlags(process: ProcessLike): void {
+  process.argv.map((arg) => {
+    if (arg === '--dev-debug') {
+      let debug = '*';
+      const filterIndex = process.argv.indexOf('--debug-filter');
+      if (filterIndex > 0) {
+        debug = process.argv[filterIndex + 1];
+
+        process.argv.splice(filterIndex, 2);
+      }
+      // convert --dev-debug into a set of environment variables
+      process.env.DEBUG = debug;
+      process.env.SF_DEBUG = '1';
+      process.env.SF_ENV = 'development';
+      process.env.SFDX_DEBUG = '1';
+      process.env.SFDX_ENV = 'development';
+
+      // need to calculate indexOf --dev-debug here because it might've changed based on --debug-filter
+      process.argv.splice(process.argv.indexOf('--dev-debug'), 1);
+    }
+  });
+}
+
+// eslint-disable-next-line @typescript-eslint/no-unsafe-member-access
+module.exports.preprocessCliFlags = preprocessCliFlags;
diff --git a/src/versions.ts b/src/versions.ts
index 4b2c7e1f..4edb8878 100644
--- a/src/versions.ts
+++ b/src/versions.ts
@@ -1,4 +1,3 @@
-/* eslint-disable */
 /*
  * Copyright (c) 2022, salesforce.com, inc.
  * All rights reserved.
@@ -8,7 +7,9 @@
 
 import * as semver from 'semver';
 // eslint-disable-next-line @typescript-eslint/no-var-requires
-const pjson = require('../package.json');
+const pjson = require('../package.json') as { engines: { node: string } };
+
+type Tag = string | semver.SemVer | null | undefined;
 
 /**
  * Determines whether or not a tag string is a semantic version.
@@ -16,13 +17,14 @@ const pjson = require('../package.json');
  * @param {*} tag The possible version string
  * @returns {boolean} True, if the string is recognized as a semantic version
  */
-export function isVersion(tag) {
+export function isVersion(tag: Tag): boolean {
   if (!tag) {
     return false;
   }
   return !!semver.valid(tag) || false;
 }
 
+// eslint-disable-next-line @typescript-eslint/no-unsafe-member-access
 module.exports.isVersion = isVersion;
 
 /**
@@ -32,7 +34,7 @@ export function checkNodeVersion(
   preferThrow = false,
   currentVersion = process.versions.node,
   requiredVersion = pjson.engines.node.slice(2)
-) {
+): void {
   if (semver.compare(currentVersion, requiredVersion) < 0) {
     const message = `Unsupported Node.js version ${currentVersion}, version ${requiredVersion} or later is required.`;
     if (!preferThrow) {
@@ -45,4 +47,5 @@ export function checkNodeVersion(
   }
 }
 
+// eslint-disable-next-line @typescript-eslint/no-unsafe-member-access
 module.exports.checkNodeVersion = checkNodeVersion;
diff --git a/test/cli.test.ts b/test/cli.test.ts
index 0a479a52..461a67ab 100644
--- a/test/cli.test.ts
+++ b/test/cli.test.ts
@@ -5,8 +5,7 @@
  * For full license text, see LICENSE.txt file in the repo root or https://opensource.org/licenses/BSD-3-Clause
  */
 // the below, there's lots of un-awaited promises for testing
-/* eslint-disable no-unused-expressions*/
-/* eslint-disable @typescript-eslint/require-await*/
+
 import { Config, Interfaces } from '@oclif/core';
 import { LoadOptions } from '@oclif/core/lib/interfaces/config';
 import { stubInterface } from '@salesforce/ts-sinon';
@@ -66,7 +65,6 @@ describe('cli', () => {
     });
 
     it('should initialize a Doctor instance when the doctor command is run', async () => {
-      debugger;
       sandbox.stub(Config.prototype, 'load').callsFake(() => Promise.resolve());
       let loadOptions: LoadOptions;
       const exec = async (argv?: string[], opts?: LoadOptions): Promise<void> => {
diff --git a/test/env.test.ts b/test/env.test.ts
index e1f30c90..54c446b6 100644
--- a/test/env.test.ts
+++ b/test/env.test.ts
@@ -5,8 +5,7 @@
  * For full license text, see LICENSE.txt file in the repo root or https://opensource.org/licenses/BSD-3-Clause
  */
 // the below, there's lots of un-awaited promises for testing
-/* eslint-disable no-unused-expressions*/
-/* eslint-disable @typescript-eslint/require-await*/
+
 import { expect } from 'chai';
 import { EnvironmentVariable } from '@salesforce/core';
 import { Env } from '../src/util/env';
diff --git a/test/flags.test.ts b/test/flags.test.ts
new file mode 100644
index 00000000..d9f61c12
--- /dev/null
+++ b/test/flags.test.ts
@@ -0,0 +1,94 @@
+/*
+ * Copyright (c) 2018, salesforce.com, inc.
+ * All rights reserved.
+ * Licensed under the BSD 3-Clause license.
+ * For full license text, see LICENSE.txt file in the repo root or https://opensource.org/licenses/BSD-3-Clause
+ */
+
+import { expect } from 'chai';
+import { preprocessCliFlags, ProcessLike } from '../src/flags';
+
+describe('CLI flags', () => {
+  it('should pass through args it does not recognize', () => {
+    const process: ProcessLike = {
+      argv: ['force:some:command', '--dev-debug', '--foo', '-f', 'bar'],
+      env: {},
+    };
+    preprocessCliFlags(process);
+    expect(process.argv).to.deep.equal(['force:some:command', '--foo', '-f', 'bar']);
+  });
+
+  it('should recognize --dev-debug', () => {
+    const process: ProcessLike = {
+      argv: ['--dev-debug'],
+      env: {},
+    };
+    preprocessCliFlags(process);
+    expect(process.argv).not.to.include('--dev-debug');
+    expect(process.env.DEBUG).to.equal('*');
+    expect(process.env.SF_DEBUG).to.equal('1');
+    expect(process.env.SF_ENV).to.equal('development');
+    expect(process.env.SFDX_DEBUG).to.equal('1');
+    expect(process.env.SFDX_ENV).to.equal('development');
+  });
+
+  it('should recognize --dev-debug in any order', () => {
+    const process: ProcessLike = {
+      argv: ['-a', 'alias', 'var=arg', '--dev-debug'],
+      env: {},
+    };
+    preprocessCliFlags(process);
+    expect(process.argv).not.to.include('--dev-debug');
+    expect(process.env.DEBUG).to.equal('*');
+    expect(process.env.SF_DEBUG).to.equal('1');
+    expect(process.env.SF_ENV).to.equal('development');
+    expect(process.env.SFDX_DEBUG).to.equal('1');
+    expect(process.env.SFDX_ENV).to.equal('development');
+    expect(process.argv.length).to.equal(3);
+  });
+
+  it('should recognize --dev-debug with a DEBUG filter', () => {
+    const process: ProcessLike = {
+      argv: ['--dev-debug', '--debug-filter', 'sf:config'],
+      env: {},
+    };
+    preprocessCliFlags(process);
+    expect(process.argv).to.deep.equal([]);
+    expect(process.argv).not.to.include('sf:Config');
+    expect(process.env.DEBUG).to.equal('sf:config');
+    expect(process.env.SF_DEBUG).to.equal('1');
+    expect(process.env.SF_ENV).to.equal('development');
+    expect(process.env.SFDX_DEBUG).to.equal('1');
+    expect(process.env.SFDX_ENV).to.equal('development');
+  });
+
+  it('should recognize --dev-debug with a DEBUG filter in any order', () => {
+    const process: ProcessLike = {
+      argv: ['--setdefault', '--debug-filter', 'sf:Config', '--dev-debug'],
+      env: {},
+    };
+    preprocessCliFlags(process);
+    expect(process.argv).to.deep.equal(['--setdefault']);
+    expect(process.argv).not.to.include('sf:Config');
+    expect(process.argv).to.include('--setdefault');
+    expect(process.env.DEBUG).to.equal('sf:Config');
+    expect(process.env.SF_DEBUG).to.equal('1');
+    expect(process.env.SF_ENV).to.equal('development');
+    expect(process.env.SFDX_DEBUG).to.equal('1');
+    expect(process.env.SFDX_ENV).to.equal('development');
+  });
+
+  it('should only set DEBUG if --dev-debug is present', () => {
+    const process: ProcessLike = {
+      argv: ['--setdefault', '--debug-filter', 'sf:Config'],
+      env: {},
+    };
+    preprocessCliFlags(process);
+    expect(process.argv).to.deep.equal(['--setdefault', '--debug-filter', 'sf:Config']);
+    expect(process.env.DEBUG).to.undefined;
+    expect(process.env.SF_DEBUG).to.be.undefined;
+    expect(process.env.SF_ENV).to.undefined;
+    expect(process.env.SFDX_DEBUG).to.undefined;
+    expect(process.env.SFDX_ENV).to.undefined;
+  });
+});