diff --git a/.changeset/fix-https-env-boolean.md b/.changeset/fix-https-env-boolean.md
new file mode 100644
index 0000000..46a04d7
--- /dev/null
+++ b/.changeset/fix-https-env-boolean.md
@@ -0,0 +1,7 @@
+---
+'maildev': patch
+---
+
+Parse `MAILDEV_HTTPS` as a boolean (#294). It was passed through as the raw
+string, so `MAILDEV_HTTPS=false` still enabled HTTPS and startup failed asking
+for `httpsCert` and `httpsKey`.
diff --git a/packages/cli/src/__tests__/config/env.test.ts b/packages/cli/src/__tests__/config/env.test.ts
index 95b048e..49bc551 100644
--- a/packages/cli/src/__tests__/config/env.test.ts
+++ b/packages/cli/src/__tests__/config/env.test.ts
@@ -101,6 +101,29 @@ describe('loadEnvConfig', () => {
     expect(config.basePathname).toBe('/mail/')
   })
 
+  it('should parse MAILDEV_HTTPS=true as boolean true', () => {
+    process.env.MAILDEV_HTTPS = 'true'
+
+    const config = loadEnvConfig()
+    expect(config.https).toBe(true)
+  })
+
+  it('should parse MAILDEV_HTTPS=false as boolean false', () => {
+    process.env.MAILDEV_HTTPS = 'false'
+
+    const config = loadEnvConfig()
+    expect(config.https).toBe(false)
+  })
+
+  it('should load MAILDEV_HTTPS_CERT and MAILDEV_HTTPS_KEY as path strings', () => {
+    process.env.MAILDEV_HTTPS_CERT = '/ssl/cert.pem'
+    process.env.MAILDEV_HTTPS_KEY = '/ssl/key.pem'
+
+    const config = loadEnvConfig()
+    expect(config.httpsCert).toBe('/ssl/cert.pem')
+    expect(config.httpsKey).toBe('/ssl/key.pem')
+  })
+
   it('should ignore invalid port numbers', () => {
     process.env.MAILDEV_SMTP_PORT = 'not-a-number'
 
diff --git a/packages/cli/src/config/env.ts b/packages/cli/src/config/env.ts
index 404d0a5..8ac3e2d 100644
--- a/packages/cli/src/config/env.ts
+++ b/packages/cli/src/config/env.ts
@@ -145,6 +145,7 @@ function envVarToConfigKey(envVar: string): keyof PartialMailDevConfig | null {
     webPort: 'web',
     incomingSecure: 'incomingSecure',
     outgoingSecure: 'outgoingSecure',
+    https: 'https',
     disableWeb: 'disableWeb',
     verbose: 'verbose',
     silent: 'silent',