diff --git a/cli/types/cypress.d.ts b/cli/types/cypress.d.ts
index 7a3120b67c11..3b83069ca80c 100644
--- a/cli/types/cypress.d.ts
+++ b/cli/types/cypress.d.ts
@@ -10,10 +10,13 @@ declare namespace Cypress {
   type PrevSubject = keyof PrevSubjectMap
   type TestingType = 'e2e' | 'component'
   type PluginConfig = (on: PluginEvents, config: PluginConfigOptions) => void | ConfigOptions | Promise<ConfigOptions>
+  interface JQueryWithSelector<TElement = HTMLElement> extends JQuery<TElement> {
+    selector?: string | null
+  }
 
   interface PrevSubjectMap<O = unknown> {
     optional: O
-    element: JQuery
+    element: JQueryWithSelector
     document: Document
     window: Window
   }
@@ -463,16 +466,18 @@ declare namespace Cypress {
     Commands: {
       add<T extends keyof Chainable>(name: T, fn: CommandFn<T>): void
       add<T extends keyof Chainable>(name: T, options: CommandOptions & {prevSubject: false}, fn: CommandFn<T>): void
+      add<T extends keyof Chainable, S = any>(name: T, options: CommandOptions & {prevSubject: true}, fn: CommandFnWithSubject<T, S>): void
       add<T extends keyof Chainable, S extends PrevSubject>(
-          name: T, options: CommandOptions & { prevSubject: true | S | ['optional'] }, fn: CommandFnWithSubject<T, PrevSubjectMap[S]>,
+          name: T, options: CommandOptions & { prevSubject: S | ['optional'] }, fn: CommandFnWithSubject<T, PrevSubjectMap[S]>,
       ): void
       add<T extends keyof Chainable, S extends PrevSubject>(
           name: T, options: CommandOptions & { prevSubject: S[] }, fn: CommandFnWithSubject<T, PrevSubjectMap<void>[S]>,
       ): void
       addAll<T extends keyof Chainable>(fns: CommandFns): void
       addAll<T extends keyof Chainable>(options: CommandOptions & {prevSubject: false}, fns: CommandFns): void
+      addAll<T extends keyof Chainable, S = any>(options: CommandOptions & { prevSubject: true }, fns: CommandFnsWithSubject<S>): void
       addAll<T extends keyof Chainable, S extends PrevSubject>(
-          options: CommandOptions & { prevSubject: true | S | ['optional'] }, fns: CommandFnsWithSubject<PrevSubjectMap[S]>,
+          options: CommandOptions & { prevSubject: S | ['optional'] }, fns: CommandFnsWithSubject<PrevSubjectMap[S]>,
       ): void
       addAll<T extends keyof Chainable, S extends PrevSubject>(
           options: CommandOptions & { prevSubject: S[] }, fns: CommandFnsWithSubject<PrevSubjectMap<void>[S]>,
diff --git a/cli/types/tests/cypress-tests.ts b/cli/types/tests/cypress-tests.ts
index a94575896245..9b5f9c0d382d 100644
--- a/cli/types/tests/cypress-tests.ts
+++ b/cli/types/tests/cypress-tests.ts
@@ -83,7 +83,7 @@ namespace CypressCommandsTests {
     arg // $ExpectType string
   })
   Cypress.Commands.add('newCommand', { prevSubject: true }, (subject, arg) => {
-    subject // $ExpectType unknown
+    subject // $ExpectType any
     arg // $ExpectType string
     return
   })
@@ -113,11 +113,11 @@ namespace CypressCommandsTests {
     arg // $ExpectType string
   })
   Cypress.Commands.add('newCommand', { prevSubject: 'element' }, (subject, arg) => {
-    subject // $ExpectType JQuery<HTMLElement>
+    subject // $ExpectType JQueryWithSelector<HTMLElement>
     arg // $ExpectType string
   })
   Cypress.Commands.add('newCommand', { prevSubject: ['element'] }, (subject, arg) => {
-    subject // $ExpectType JQuery<HTMLElement>
+    subject // $ExpectType JQueryWithSelector<HTMLElement>
     arg // $ExpectType string
   })
   Cypress.Commands.add('newCommand', { prevSubject: ['element', 'document', 'window'] }, (subject, arg) => {
@@ -126,7 +126,7 @@ namespace CypressCommandsTests {
     } else if (subject instanceof Document) {
       subject // $ExpectType Document
     } else {
-      subject // $ExpectType JQuery<HTMLElement>
+      subject // $ExpectType JQueryWithSelector<HTMLElement>
     }
     arg // $ExpectType string
   })
@@ -136,7 +136,7 @@ namespace CypressCommandsTests {
     } else if (subject instanceof Document) {
       subject // $ExpectType Document
     } else if (subject) {
-      subject // $ExpectType JQuery<HTMLElement>
+      subject // $ExpectType JQueryWithSelector<HTMLElement>
     } else {
       subject // $ExpectType void
     }
@@ -173,7 +173,7 @@ namespace CypressCommandsTests {
   })
   Cypress.Commands.addAll({ prevSubject: true }, {
     newCommand: (subject, arg) => {
-      subject // $ExpectType unknown
+      subject // $ExpectType any
       arg // $ExpectType any
       return
     },
@@ -215,13 +215,13 @@ namespace CypressCommandsTests {
   })
   Cypress.Commands.addAll({ prevSubject: 'element' }, {
     newCommand: (subject, arg) => {
-      subject // $ExpectType JQuery<HTMLElement>
+      subject // $ExpectType JQueryWithSelector<HTMLElement>
       arg // $ExpectType any
     }
   })
   Cypress.Commands.addAll({ prevSubject: ['element'] }, {
     newCommand: (subject, arg) => {
-      subject // $ExpectType JQuery<HTMLElement>
+      subject // $ExpectType JQueryWithSelector<HTMLElement>
       arg // $ExpectType any
     }
   })
@@ -232,7 +232,7 @@ namespace CypressCommandsTests {
       } else if (subject instanceof Document) {
         subject // $ExpectType Document
       } else {
-        subject // $ExpectType JQuery<HTMLElement>
+        subject // $ExpectType JQueryWithSelector<HTMLElement>
       }
       arg // $ExpectType any
     }
@@ -244,7 +244,7 @@ namespace CypressCommandsTests {
       } else if (subject instanceof Document) {
         subject // $ExpectType Document
       } else if (subject) {
-        subject // $ExpectType JQuery<HTMLElement>
+        subject // $ExpectType JQueryWithSelector<HTMLElement>
       } else {
         subject // $ExpectType void
       }
@@ -271,7 +271,7 @@ namespace CypressCommandsTests {
     originalFn.apply(this, [arg]) // $ExpectType Chainable<number>
   })
   Cypress.Commands.overwrite<'type', 'element'>('type', (originalFn, element, text, options?: Partial<Cypress.TypeOptions & {sensitive: boolean}>) => {
-    element // $ExpectType JQuery<HTMLElement>
+    element // $ExpectType JQueryWithSelector<HTMLElement>
     text // $ExpectType string
 
     if (options && options.sensitive) {