diff --git a/cli/types/cypress.d.ts b/cli/types/cypress.d.ts
index dde1a928b7..11aa72dd2d 100644
--- a/cli/types/cypress.d.ts
+++ b/cli/types/cypress.d.ts
@@ -492,6 +492,10 @@ declare namespace Cypress {
   }
 
   type CanReturnChainable = void | Chainable
+  type ThenReturn<S, R> =
+    R extends void ? Chainable<S> :
+    R extends R | undefined ? Chainable<S | Exclude<R, undefined>> :
+    Chainable<S>
 
   /**
    * Chainable interface for non-array Subjects
@@ -1751,12 +1755,24 @@ declare namespace Cypress {
      * @see https://on.cypress.io/then
      */
     then<S extends object | any[] | string | number | boolean>(fn: (this: ObjectLike, currentSubject: Subject) => S): Chainable<S>
+    /**
+     * Enables you to work with the subject yielded from the previous command / promise.
+     *
+     * @see https://on.cypress.io/then
+     */
+    then<S>(fn: (this: ObjectLike, currentSubject: Subject) => S): ThenReturn<Subject, S>
     /**
      * Enables you to work with the subject yielded from the previous command / promise.
      *
      * @see https://on.cypress.io/then
      */
     then<S extends object | any[] | string | number | boolean>(options: Partial<Timeoutable>, fn: (this: ObjectLike, currentSubject: Subject) => S): Chainable<S>
+    /**
+     * Enables you to work with the subject yielded from the previous command / promise.
+     *
+     * @see https://on.cypress.io/then
+     */
+    then<S>(options: Partial<Timeoutable>, fn: (this: ObjectLike, currentSubject: Subject) => S): ThenReturn<Subject, S>
     /**
      * Enables you to work with the subject yielded from the previous command.
      *
diff --git a/cli/types/tests/cypress-tests.ts b/cli/types/tests/cypress-tests.ts
index ccc8e1cba7..a116041136 100644
--- a/cli/types/tests/cypress-tests.ts
+++ b/cli/types/tests/cypress-tests.ts
@@ -179,6 +179,25 @@ cy.wrap(['bar', 'baz'])
   })
 
 describe('then', () => {
+  // https://github.com/cypress-io/cypress/issues/5575
+  it('should respect the return type of callback', () => {
+    // Expected type is verbose here because the function below matches 2 declarations.
+    // * then<S extends object | any[] | string | number | boolean>(fn: (this: ObjectLike, currentSubject: Subject) => S): Chainable<S>
+    // * then<S>(fn: (this: ObjectLike, currentSubject: Subject) => S): ThenReturn<Subject, S>
+    // For our purpose, it doesn't matter.
+    const result = cy.get('foo').then(el => el.attr('foo'))
+    result // $ExpectType Chainable<JQuery<HTMLElement>> | Chainable<string | JQuery<HTMLElement>>
+
+    const result2 = cy.get('foo').then(el => `${el}`)
+    result2 // $ExpectType Chainable<string>
+
+    const result3 = cy.get('foo').then({ timeout: 1234 }, el => el.attr('foo'))
+    result3 // $ExpectType Chainable<JQuery<HTMLElement>> | Chainable<string | JQuery<HTMLElement>>
+
+    const result4 = cy.get('foo').then({ timeout: 1234 }, el => `${el}`)
+    result4 // $ExpectType Chainable<string>
+  })
+
   it('should have the correct type signature', () => {
     cy.wrap({ foo: 'bar' })
       .then(s => {