diff --git a/.changeset/dry-tips-burn.md b/.changeset/dry-tips-burn.md
new file mode 100644
index 00000000..f867a420
--- /dev/null
+++ b/.changeset/dry-tips-burn.md
@@ -0,0 +1,5 @@
+---
+'eslint-plugin-primer-react': minor
+---
+
+Add use-deprecated-from-deprecated rule
diff --git a/docs/rules/use-deprecated-from-deprecated.md b/docs/rules/use-deprecated-from-deprecated.md
new file mode 100644
index 00000000..01036ded
--- /dev/null
+++ b/docs/rules/use-deprecated-from-deprecated.md
@@ -0,0 +1,25 @@
+# Use Deprecated from Deprecated
+
+## Rule Details
+
+This rule enforces the usage of deprecated imports from `@primer/react/deprecated`.
+
+👎 Examples of **incorrect** code for this rule
+
+```jsx
+import {Dialog} from '@primer/react'
+
+function ExampleComponent() {
+  return <Dialog>{/* ... */}</Dialog>
+}
+```
+
+👍 Examples of **correct** code for this rule:
+
+```jsx
+import {Dialog} from '@primer/react/deprecated'
+
+function ExampleComponent() {
+  return <Dialog>{/* ... */}</Dialog>
+}
+```
diff --git a/src/index.js b/src/index.js
index 20e1fb01..d9ce57df 100644
--- a/src/index.js
+++ b/src/index.js
@@ -10,6 +10,7 @@ module.exports = {
     'a11y-link-in-text-block': require('./rules/a11y-link-in-text-block'),
     'a11y-remove-disable-tooltip': require('./rules/a11y-remove-disable-tooltip'),
     'a11y-use-next-tooltip': require('./rules/a11y-use-next-tooltip'),
+    'use-deprecated-from-deprecated': require('./rules/use-deprecated-from-deprecated'),
   },
   configs: {
     recommended: require('./configs/recommended'),
diff --git a/src/rules/__tests__/use-deprecated-from-deprecated.test.js b/src/rules/__tests__/use-deprecated-from-deprecated.test.js
new file mode 100644
index 00000000..2b3cbd98
--- /dev/null
+++ b/src/rules/__tests__/use-deprecated-from-deprecated.test.js
@@ -0,0 +1,66 @@
+'use strict'
+
+const {RuleTester} = require('eslint')
+const rule = require('../use-deprecated-from-deprecated')
+
+const ruleTester = new RuleTester({
+  parserOptions: {
+    ecmaVersion: 'latest',
+    sourceType: 'module',
+    ecmaFeatures: {
+      jsx: true,
+    },
+  },
+})
+
+ruleTester.run('use-deprecated-from-deprecated', rule, {
+  valid: [],
+  invalid: [
+    // Single deprecated import
+    {
+      code: `import {Tooltip} from '@primer/react'`,
+      output: `import {Tooltip} from '@primer/react/deprecated'`,
+      errors: ['Import deprecated components from @primer/react/deprecated'],
+    },
+
+    // Single deprecated import with existing deprecated entrypoint
+    {
+      code: `import {Tooltip} from '@primer/react'
+import {Dialog} from '@primer/react/deprecated'`,
+      output: `\nimport {Dialog, Tooltip} from '@primer/react/deprecated'`,
+      errors: ['Import deprecated components from @primer/react/deprecated'],
+    },
+
+    // Multiple deprecated imports
+    {
+      code: `import {Dialog, Tooltip} from '@primer/react'`,
+      output: `import {Dialog, Tooltip} from '@primer/react/deprecated'`,
+      errors: ['Import deprecated components from @primer/react/deprecated'],
+    },
+
+    // Mixed deprecated and non-deprecated imports
+    {
+      code: `import {Button, Tooltip} from '@primer/react'`,
+      output: `import {Button, } from '@primer/react'
+import {Tooltip} from '@primer/react/deprecated'`,
+      errors: ['Import deprecated components from @primer/react/deprecated'],
+    },
+
+    // Mixed deprecated and non-deprecated imports with existing deprecated
+    {
+      code: `import {Button, Tooltip} from '@primer/react'
+import {Dialog} from '@primer/react/deprecated'`,
+      output: `import {Button, } from '@primer/react'
+import {Dialog, Tooltip} from '@primer/react/deprecated'`,
+      errors: ['Import deprecated components from @primer/react/deprecated'],
+    },
+
+    // Multiple mixed deprecated and non-deprecated imports
+    {
+      code: `import {Button, Dialog, Tooltip} from '@primer/react'`,
+      output: `import {Button,  } from '@primer/react'
+import {Dialog, Tooltip} from '@primer/react/deprecated'`,
+      errors: ['Import deprecated components from @primer/react/deprecated'],
+    },
+  ],
+})
diff --git a/src/rules/use-deprecated-from-deprecated.js b/src/rules/use-deprecated-from-deprecated.js
new file mode 100644
index 00000000..5b6c220c
--- /dev/null
+++ b/src/rules/use-deprecated-from-deprecated.js
@@ -0,0 +1,130 @@
+'use strict'
+
+const url = require('../url')
+
+const components = [
+  {
+    identifier: 'Dialog',
+    entrypoint: '@primer/react',
+  },
+  {
+    identifier: 'Octicon',
+    entrypoint: '@primer/react',
+  },
+  {
+    identifier: 'Pagehead',
+    entrypoint: '@primer/react',
+  },
+  {
+    identifier: 'TabNav',
+    entrypoint: '@primer/react',
+  },
+  {
+    identifier: 'Tooltip',
+    entrypoint: '@primer/react',
+  },
+]
+
+const entrypoints = new Map()
+
+for (const component of components) {
+  if (!entrypoints.has(component.entrypoint)) {
+    entrypoints.set(component.entrypoint, new Set())
+  }
+  entrypoints.get(component.entrypoint).add(component.identifier)
+}
+
+/**
+ * @type {import('eslint').Rule.RuleModule}
+ */
+module.exports = {
+  meta: {
+    type: 'problem',
+    docs: {
+      description: 'Use deprecated components from the `@primer/react/deprecated` entrypoint',
+      recommended: true,
+      url: url(module),
+    },
+    fixable: true,
+    schema: [],
+  },
+  create(context) {
+    const sourceCode = context.getSourceCode()
+
+    return {
+      ImportDeclaration(node) {
+        if (!entrypoints.has(node.source.value)) {
+          return
+        }
+
+        const entrypoint = entrypoints.get(node.source.value)
+        const deprecated = node.specifiers.filter(specifier => {
+          return entrypoint.has(specifier.imported.name)
+        })
+
+        if (deprecated.length === 0) {
+          return
+        }
+
+        const deprecatedEntrypoint = node.parent.body.find(node => {
+          if (node.type !== 'ImportDeclaration') {
+            return false
+          }
+
+          return node.source.value === '@primer/react/deprecated'
+        })
+
+        // All imports are deprecated
+        if (deprecated.length === node.specifiers.length) {
+          context.report({
+            node,
+            message: 'Import deprecated components from @primer/react/deprecated',
+            *fix(fixer) {
+              if (deprecatedEntrypoint) {
+                const lastSpecifier = deprecatedEntrypoint.specifiers[deprecatedEntrypoint.specifiers.length - 1]
+
+                yield fixer.remove(node)
+                yield fixer.insertTextAfter(
+                  lastSpecifier,
+                  `, ${node.specifiers.map(specifier => specifier.imported.name).join(', ')}`,
+                )
+              } else {
+                yield fixer.replaceText(node.source, `'@primer/react/deprecated'`)
+              }
+            },
+          })
+        } else {
+          // There is a mix of deprecated and non-deprecated imports
+          context.report({
+            node,
+            message: 'Import deprecated components from @primer/react/deprecated',
+            *fix(fixer) {
+              for (const specifier of deprecated) {
+                yield fixer.remove(specifier)
+                const comma = sourceCode.getTokenAfter(specifier)
+                if (comma.value === ',') {
+                  yield fixer.remove(comma)
+                }
+              }
+
+              if (deprecatedEntrypoint) {
+                const lastSpecifier = deprecatedEntrypoint.specifiers[deprecatedEntrypoint.specifiers.length - 1]
+                yield fixer.insertTextAfter(
+                  lastSpecifier,
+                  `, ${deprecated.map(specifier => specifier.imported.name).join(', ')}`,
+                )
+              } else {
+                yield fixer.insertTextAfter(
+                  node,
+                  `\nimport {${deprecated
+                    .map(specifier => specifier.imported.name)
+                    .join(', ')}} from '@primer/react/deprecated'`,
+                )
+              }
+            },
+          })
+        }
+      },
+    }
+  },
+}