diff --git a/packages/cli-helpers/package.json b/packages/cli-helpers/package.json
index 8ebb15ecc338..f48fec629930 100644
--- a/packages/cli-helpers/package.json
+++ b/packages/cli-helpers/package.json
@@ -24,11 +24,13 @@
   "dependencies": {
     "@babel/core": "^7.22.20",
     "@babel/runtime-corejs3": "7.23.1",
+    "@iarna/toml": "2.2.5",
     "@opentelemetry/api": "1.4.1",
     "@redwoodjs/project-config": "6.0.7",
     "@redwoodjs/telemetry": "6.0.7",
     "chalk": "4.1.2",
     "core-js": "3.32.2",
+    "dotenv": "16.3.1",
     "execa": "5.1.1",
     "listr2": "6.6.1",
     "lodash": "4.17.21",
diff --git a/packages/cli-helpers/src/lib/__tests__/__snapshots__/project.test.ts.snap b/packages/cli-helpers/src/lib/__tests__/__snapshots__/project.test.ts.snap
new file mode 100644
index 000000000000..6da535eaf61e
--- /dev/null
+++ b/packages/cli-helpers/src/lib/__tests__/__snapshots__/project.test.ts.snap
@@ -0,0 +1,149 @@
+// Jest Snapshot v1, https://goo.gl/fbAQLP
+
+exports[`addEnvVar addEnvVar adds environment variables as part of a setup task should add a comment that the existing environment variable value was not changed, but include its new value as a comment 1`] = `
+"EXISTING_VAR=value
+# CommentedVar=123
+
+# Note: The existing environment variable EXISTING_VAR was not overwritten. Uncomment to use its new value.
+# Updated existing variable Comment
+# EXISTING_VAR = new_value
+"
+`;
+
+exports[`addEnvVar addEnvVar adds environment variables as part of a setup task should add a new environment variable when it does not exist 1`] = `
+"EXISTING_VAR = value
+# CommentedVar = 123
+
+# New Variable Comment
+NEW_VAR = new_value
+"
+`;
+
+exports[`addEnvVar addEnvVar adds environment variables as part of a setup task should add a new environment variable when it does not exist when existing envars have no spacing 1`] = `
+"EXISTING_VAR=value
+# CommentedVar = 123
+
+# New Variable Comment
+NEW_VAR = new_value
+"
+`;
+
+exports[`addEnvVar addEnvVar adds environment variables as part of a setup task should handle existing environment variables and new value with quoted values by not updating the original value 1`] = `
+"EXISTING_VAR = "value"
+# CommentedVar = 123
+
+# Note: The existing environment variable EXISTING_VAR was not overwritten. Uncomment to use its new value.
+# New Variable Comment
+# EXISTING_VAR = new_value
+"
+`;
+
+exports[`addEnvVar addEnvVar adds environment variables as part of a setup task should handle existing environment variables with quoted values 1`] = `
+"EXISTING_VAR = "value"
+# CommentedVar = 123
+"
+`;
+
+exports[`addEnvVar addEnvVar adds environment variables as part of a setup task should handle existing environment variables with quoted values and no spacing 1`] = `
+"EXISTING_VAR="value"
+# CommentedVar=123
+"
+`;
+
+exports[`updateTomlConfig updateTomlConfig configures a new CLI plugin adds package but keeps autoInstall false 1`] = `
+"[web]
+title = "Redwood App"
+port = 8_910
+apiUrl = "/.redwood/functions"
+includeEnvironmentVariables = [ ]
+
+[api]
+port = 8_911
+
+[experimental.cli]
+autoInstall = false
+
+[[experimental.cli.plugins]]
+package = "@example/test-package-when-autoInstall-false"
+enabled = true
+"
+`;
+
+exports[`updateTomlConfig updateTomlConfig configures a new CLI plugin adds when experimental cli has some plugins configured 1`] = `
+"[web]
+title = "Redwood App"
+port = 8_910
+apiUrl = "/.redwood/functions"
+includeEnvironmentVariables = [ ]
+
+[api]
+port = 8_911
+
+[experimental.cli]
+autoInstall = true
+
+  [[experimental.cli.plugins]]
+  package = "@existing-example/some-package-when-cli-has-some-packages-configured"
+
+[[experimental.cli.plugins]]
+package = "@example/test-package-name"
+enabled = true
+"
+`;
+
+exports[`updateTomlConfig updateTomlConfig configures a new CLI plugin adds when experimental cli is not configured 1`] = `
+"[web]
+title = "Redwood App"
+port = 8_910
+apiUrl = "/.redwood/functions"
+includeEnvironmentVariables = [ ]
+
+[api]
+port = 8_911
+
+[experimental.cli]
+autoInstall = true
+
+  [[experimental.cli.plugins]]
+  package = "@example/test-package-when-cli-not-configured"
+  enabled = true
+"
+`;
+
+exports[`updateTomlConfig updateTomlConfig configures a new CLI plugin adds when experimental cli is setup but has no plugins configured 1`] = `
+"[web]
+title = "Redwood App"
+port = 8_910
+apiUrl = "/.redwood/functions"
+includeEnvironmentVariables = [ ]
+
+[api]
+port = 8_911
+
+[experimental.cli]
+autoInstall = true
+
+[[experimental.cli.plugins]]
+package = "@example/test-package-when-no-plugins-configured"
+enabled = true
+"
+`;
+
+exports[`updateTomlConfig updateTomlConfig configures a new CLI plugin does not add duplicate place when experimental cli has that plugin configured 1`] = `
+"[web]
+title = "Redwood App"
+port = 8_910
+apiUrl = "/.redwood/functions"
+includeEnvironmentVariables = [ ]
+
+[api]
+port = 8_911
+
+[experimental.cli]
+autoInstall = true
+
+  [[experimental.cli.plugins]]
+  package = "@existing-example/some-package-name-already-exists"
+
+"
+`;
diff --git a/packages/cli-helpers/src/lib/__tests__/project.test.ts b/packages/cli-helpers/src/lib/__tests__/project.test.ts
new file mode 100644
index 000000000000..3aef810bc9bc
--- /dev/null
+++ b/packages/cli-helpers/src/lib/__tests__/project.test.ts
@@ -0,0 +1,214 @@
+import fs from 'fs'
+
+import toml from '@iarna/toml'
+
+import { updateTomlConfig, addEnvVar } from '../project' // Replace with the correct path to your module
+
+jest.mock('fs')
+
+const defaultRedwoodToml = {
+  web: {
+    title: 'Redwood App',
+    port: 8910,
+    apiUrl: '/.redwood/functions',
+    includeEnvironmentVariables: [],
+  },
+  api: {
+    port: 8911,
+  },
+}
+
+const getRedwoodToml = () => {
+  return defaultRedwoodToml
+}
+
+jest.mock('@redwoodjs/project-config', () => {
+  return {
+    getPaths: () => {
+      return {
+        generated: {
+          base: '.redwood',
+        },
+        base: '',
+      }
+    },
+    getConfigPath: () => {
+      return '.redwood.toml'
+    },
+    getConfig: () => {
+      return getRedwoodToml()
+    },
+  }
+})
+
+describe('addEnvVar', () => {
+  let envFileContent = ''
+
+  describe('addEnvVar adds environment variables as part of a setup task', () => {
+    beforeEach(() => {
+      jest.spyOn(fs, 'existsSync').mockImplementation(() => {
+        return true
+      })
+
+      jest.spyOn(fs, 'readFileSync').mockImplementation(() => {
+        return envFileContent
+      })
+
+      jest.spyOn(fs, 'writeFileSync').mockImplementation((envPath, envFile) => {
+        expect(envPath).toContain('.env')
+        return envFile
+      })
+    })
+
+    afterEach(() => {
+      jest.restoreAllMocks()
+      envFileContent = ''
+    })
+
+    it('should add a new environment variable when it does not exist', () => {
+      envFileContent = 'EXISTING_VAR = value\n# CommentedVar = 123\n'
+      const file = addEnvVar('NEW_VAR', 'new_value', 'New Variable Comment')
+
+      expect(file).toMatchSnapshot()
+    })
+
+    it('should add a new environment variable when it does not exist when existing envars have no spacing', () => {
+      envFileContent = 'EXISTING_VAR=value\n# CommentedVar = 123\n'
+      const file = addEnvVar('NEW_VAR', 'new_value', 'New Variable Comment')
+
+      expect(file).toMatchSnapshot()
+    })
+
+    it('should add a comment that the existing environment variable value was not changed, but include its new value as a comment', () => {
+      envFileContent = 'EXISTING_VAR=value\n# CommentedVar=123\n'
+      const file = addEnvVar(
+        'EXISTING_VAR',
+        'new_value',
+        'Updated existing variable Comment'
+      )
+
+      expect(file).toMatchSnapshot()
+    })
+
+    it('should handle existing environment variables with quoted values', () => {
+      envFileContent = `EXISTING_VAR = "value"\n# CommentedVar = 123\n`
+      const file = addEnvVar('EXISTING_VAR', 'value', 'New Variable Comment')
+
+      expect(file).toMatchSnapshot()
+    })
+
+    it('should handle existing environment variables with quoted values and no spacing', () => {
+      envFileContent = `EXISTING_VAR="value"\n# CommentedVar=123\n`
+      const file = addEnvVar('EXISTING_VAR', 'value', 'New Variable Comment')
+
+      expect(file).toMatchSnapshot()
+    })
+
+    it('should handle existing environment variables and new value with quoted values by not updating the original value', () => {
+      envFileContent = `EXISTING_VAR = "value"\n# CommentedVar = 123\n`
+      const file = addEnvVar(
+        'EXISTING_VAR',
+        'new_value',
+        'New Variable Comment'
+      )
+
+      expect(file).toMatchSnapshot()
+    })
+  })
+})
+
+describe('updateTomlConfig', () => {
+  describe('updateTomlConfig configures a new CLI plugin', () => {
+    beforeEach(() => {
+      jest.spyOn(fs, 'existsSync').mockImplementation(() => {
+        return true
+      })
+
+      jest.spyOn(fs, 'readFileSync').mockImplementation(() => {
+        return toml.stringify(defaultRedwoodToml)
+      })
+
+      jest
+        .spyOn(fs, 'writeFileSync')
+        .mockImplementation((tomlPath, tomlFile) => {
+          expect(tomlPath).toContain('redwood.toml')
+          return tomlFile
+        })
+    })
+
+    afterEach(() => {
+      jest.restoreAllMocks()
+    })
+
+    it('adds when experimental cli is not configured', () => {
+      const file = updateTomlConfig(
+        '@example/test-package-when-cli-not-configured'
+      )
+      expect(file).toMatchSnapshot()
+    })
+
+    it('adds when experimental cli has some plugins configured', () => {
+      defaultRedwoodToml['experimental'] = {
+        cli: {
+          autoInstall: true,
+          plugins: [
+            {
+              package:
+                '@existing-example/some-package-when-cli-has-some-packages-configured',
+            },
+          ],
+        },
+      }
+
+      const file = updateTomlConfig('@example/test-package-name')
+      expect(file).toMatchSnapshot()
+    })
+
+    it('adds when experimental cli is setup but has no plugins configured', () => {
+      defaultRedwoodToml['experimental'] = {
+        cli: {
+          autoInstall: true,
+        },
+      }
+
+      const file = updateTomlConfig(
+        '@example/test-package-when-no-plugins-configured'
+      )
+
+      expect(file).toMatchSnapshot()
+    })
+
+    it('adds package but keeps autoInstall false', () => {
+      defaultRedwoodToml['experimental'] = {
+        cli: {
+          autoInstall: false,
+        },
+      }
+
+      const file = updateTomlConfig(
+        '@example/test-package-when-autoInstall-false'
+      )
+
+      expect(file).toMatchSnapshot()
+    })
+
+    it('does not add duplicate place when experimental cli has that plugin configured', () => {
+      defaultRedwoodToml['experimental'] = {
+        cli: {
+          autoInstall: true,
+          plugins: [
+            {
+              package: '@existing-example/some-package-name-already-exists',
+            },
+          ],
+        },
+      }
+
+      const file = updateTomlConfig(
+        '@existing-example/some-package-name-already-exists'
+      )
+
+      expect(file).toMatchSnapshot()
+    })
+  })
+})
diff --git a/packages/cli-helpers/src/lib/project.ts b/packages/cli-helpers/src/lib/project.ts
index 1e0c6fe618dd..7755671f2aad 100644
--- a/packages/cli-helpers/src/lib/project.ts
+++ b/packages/cli-helpers/src/lib/project.ts
@@ -1,7 +1,16 @@
 import fs from 'fs'
 import path from 'path'
 
-import { resolveFile, findUp } from '@redwoodjs/project-config'
+import type { JsonMap } from '@iarna/toml'
+import toml from '@iarna/toml'
+import dotenv from 'dotenv'
+
+import {
+  findUp,
+  getConfigPath,
+  getConfig,
+  resolveFile,
+} from '@redwoodjs/project-config'
 
 import { colors } from './colors'
 import { getPaths } from './paths'
@@ -33,21 +42,117 @@ export const getInstalledRedwoodVersion = () => {
   }
 }
 
+/**
+ * Updates the project's redwood.toml file to include the specified packages plugin
+ *
+ * Uses toml parsing to determine if the plugin is already included in the file and
+ * only adds it if it is not.
+ *
+ * Writes the updated config to the file system by appending strings, not stringify-ing the toml.
+ */
+export const updateTomlConfig = (packageName: string) => {
+  const redwoodTomlPath = getConfigPath()
+  const originalTomlContent = fs.readFileSync(redwoodTomlPath, 'utf-8')
+
+  let tomlToAppend = {} as JsonMap
+
+  const config = getConfig(redwoodTomlPath)
+
+  const cliSection = config.experimental?.cli
+
+  if (!cliSection) {
+    tomlToAppend = {
+      experimental: {
+        cli: {
+          autoInstall: true,
+          plugins: [{ package: packageName, enabled: true }],
+        },
+      },
+    }
+  } else if (cliSection.plugins) {
+    const packageExists = cliSection.plugins.some(
+      (plugin) => plugin.package === packageName
+    )
+
+    if (!packageExists) {
+      tomlToAppend = {
+        experimental: {
+          cli: {
+            plugins: [{ package: packageName, enabled: true }],
+          },
+        },
+      }
+    }
+  } else {
+    tomlToAppend = {
+      experimental: {
+        cli: {
+          plugins: [{ package: packageName, enabled: true }],
+        },
+      },
+    }
+  }
+
+  const newConfig = originalTomlContent + '\n' + toml.stringify(tomlToAppend)
+
+  return fs.writeFileSync(redwoodTomlPath, newConfig, 'utf-8')
+}
+
+export const updateTomlConfigTask = (packageName: string) => {
+  return {
+    title: `Updating redwood.toml to configure ${packageName} ...`,
+    task: () => {
+      updateTomlConfig(packageName)
+    },
+  }
+}
+
 export const addEnvVarTask = (name: string, value: string, comment: string) => {
   return {
     title: `Adding ${name} var to .env...`,
     task: () => {
-      const envPath = path.join(getPaths().base, '.env')
-      const content = [comment && `# ${comment}`, `${name}=${value}`, ''].flat()
-      let envFile = ''
+      addEnvVar(name, value, comment)
+    },
+  }
+}
 
-      if (fs.existsSync(envPath)) {
-        envFile = fs.readFileSync(envPath).toString() + '\n'
-      }
+export const addEnvVar = (name: string, value: string, comment: string) => {
+  const envPath = path.join(getPaths().base, '.env')
+  let envFile = ''
+  const newEnvironmentVariable = [
+    comment && `# ${comment}`,
+    `${name} = ${value}`,
+    '',
+  ]
+    .flat()
+    .join('\n')
 
-      fs.writeFileSync(envPath, envFile + content.join('\n'))
-    },
+  if (fs.existsSync(envPath)) {
+    envFile = fs.readFileSync(envPath).toString()
+    const existingEnvVars = dotenv.parse(envFile)
+
+    if (existingEnvVars[name] && existingEnvVars[name] === value) {
+      return envFile
+    }
+
+    if (existingEnvVars[name]) {
+      const p = [
+        `# Note: The existing environment variable ${name} was not overwritten. Uncomment to use its new value.`,
+        comment && `# ${comment}`,
+        `# ${name} = ${value}`,
+        '',
+      ]
+        .flat()
+        .join('\n')
+      envFile += '\n' + p
+    } else {
+      envFile += '\n' + newEnvironmentVariable
+    }
+  } else {
+    envFile = newEnvironmentVariable
   }
+
+  return fs.writeFileSync(envPath, envFile)
 }
 
 /**
diff --git a/yarn.lock b/yarn.lock
index 601bcc027e52..d512c826da04 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -8392,6 +8392,7 @@ __metadata:
     "@babel/cli": 7.23.0
     "@babel/core": ^7.22.20
     "@babel/runtime-corejs3": 7.23.1
+    "@iarna/toml": 2.2.5
     "@opentelemetry/api": 1.4.1
     "@redwoodjs/project-config": 6.0.7
     "@redwoodjs/telemetry": 6.0.7
@@ -8400,6 +8401,7 @@ __metadata:
     "@types/yargs": 17.0.24
     chalk: 4.1.2
     core-js: 3.32.2
+    dotenv: 16.3.1
     execa: 5.1.1
     jest: 29.7.0
     listr2: 6.6.1