diff --git a/packages/driver/cypress/integration/commands/actions/click_spec.js b/packages/driver/cypress/integration/commands/actions/click_spec.js
index 634023a705ab..a566f9544bdb 100644
--- a/packages/driver/cypress/integration/commands/actions/click_spec.js
+++ b/packages/driver/cypress/integration/commands/actions/click_spec.js
@@ -752,6 +752,20 @@ describe('src/cy/commands/actions/click', () => {
       })
     })
 
+    it('each click gets a full command timeout', () => {
+      cy.spy(cy, 'retry')
+
+      cy.get('#three-buttons button').click({ multiple: true }).then(() => {
+        const [firstCall, secondCall] = cy.retry.getCalls()
+        const firstCallOptions = firstCall.args[1]
+        const secondCallOptions = secondCall.args[1]
+
+        // ensure we clone the options object passed to `retry()` so that
+        // each click in `{ multiple: true }` gets its own full timeout
+        expect(firstCallOptions !== secondCallOptions, 'Expected click retry options to be different object references between clicks').to.be.true
+      })
+    })
+
     // this test needs to increase the height + width of the div
     // when we implement scrollBy the delta of the left/top
     it('can click elements which are huge and the center is naturally below the fold', () => {
diff --git a/packages/driver/src/cy/actionability.js b/packages/driver/src/cy/actionability.js
index da4dd01f4c7c..1426ec7079f7 100644
--- a/packages/driver/src/cy/actionability.js
+++ b/packages/driver/src/cy/actionability.js
@@ -261,16 +261,29 @@ const getCoordinatesForEl = function (cy, $el, options) {
 }
 
 const ensureNotAnimating = function (cy, $el, coordsHistory, animationDistanceThreshold) {
-  // if we dont have at least 2 points
-  // then automatically retry
+  // if we dont have at least 2 points, we throw this error to force a
+  // retry, which will get us another point.
+  // this error is purposefully generic because if the actionability
+  //check times out, this error is the one displayed to the user and
+  // saying something like "coordsHistory must be at least 2 sets
+  // of coords" is not very useful.
+  // that would only happen if the actionability check times out, which
+  // shouldn't happen with default timeouts, but could theoretically
+  // on a very, very slow system
+  // https://github.com/cypress-io/cypress/issues/3738
   if (coordsHistory.length < 2) {
-    $errUtils.throwErrByPath('dom.animation_coords_history_invalid')
+    $errUtils.throwErrByPath('dom.actionability_failed', {
+      args: {
+        node: $dom.stringify($el),
+        cmd: cy.state('current').get('name'),
+      },
+    })
   }
 
   // verify that our element is not currently animating
   // by verifying it is still at the same coordinates within
   // 5 pixels of x/y
-  return cy.ensureElementIsNotAnimating($el, coordsHistory, animationDistanceThreshold)
+  cy.ensureElementIsNotAnimating($el, coordsHistory, animationDistanceThreshold)
 }
 
 const verify = function (cy, $el, options, callbacks) {
@@ -336,7 +349,6 @@ const verify = function (cy, $el, options, callbacks) {
   }
 
   return Promise.try(() => {
-    let retryActionability
     const coordsHistory = []
 
     const runAllChecks = function () {
@@ -426,7 +438,7 @@ const verify = function (cy, $el, options, callbacks) {
     // element passes every single check, we MUST fire the event
     // synchronously else we risk the state changing between
     // the checks and firing the event!
-    return (retryActionability = function () {
+    const retryActionability = () => {
       try {
         return runAllChecks()
       } catch (err) {
@@ -434,7 +446,9 @@ const verify = function (cy, $el, options, callbacks) {
 
         return cy.retry(retryActionability, options)
       }
-    })()
+    }
+
+    return retryActionability()
   })
 }
 
diff --git a/packages/driver/src/cy/commands/actions/click.js b/packages/driver/src/cy/commands/actions/click.js
index 3d74cbb868c3..cb56c8fab5d3 100644
--- a/packages/driver/src/cy/commands/actions/click.js
+++ b/packages/driver/src/cy/commands/actions/click.js
@@ -116,9 +116,8 @@ module.exports = (Commands, Cypress, cy, state, config) => {
         })
       }
 
-      // we want to add this delay delta to our
-      // runnables timeout so we prevent it from
-      // timing out from multiple clicks
+      // add this delay delta to the runnables timeout because we delay
+      // by it below before performing each click
       cy.timeout($actionability.delay, true, eventName)
 
       const createLog = (domEvents, fromElWindow, fromAutWindow) => {
@@ -169,11 +168,17 @@ module.exports = (Commands, Cypress, cy, state, config) => {
         .return(null)
       }
 
+      // if { multiple: true }, make a shallow copy of options, since
+      // properties like `total` and `_retries` are mutated by
+      // $actionability.verify and retrying, but each click should
+      // have its own full timeout
+      const individualOptions = { ... options }
+
       // must use callbacks here instead of .then()
       // because we're issuing the clicks synchronously
       // once we establish the coordinates and the element
       // passes all of the internal checks
-      return $actionability.verify(cy, $el, options, {
+      return $actionability.verify(cy, $el, individualOptions, {
         onScroll ($el, type) {
           return Cypress.action('cy:scrolled', $el, type)
         },
diff --git a/packages/driver/src/cypress/error_messages.js b/packages/driver/src/cypress/error_messages.js
index 0b9082516c1d..dfbb903c9dad 100644
--- a/packages/driver/src/cypress/error_messages.js
+++ b/packages/driver/src/cypress/error_messages.js
@@ -293,6 +293,13 @@ module.exports = {
   },
 
   dom: {
+    actionability_failed: stripIndent`
+      ${cmd('{{cmd}}')} could not be issued because we could not determine the actionability of this element:
+
+      \`{{node}}\`
+
+      You can prevent this by passing \`{force: true}\` to disable all error checking.
+    `,
     animating: {
       message: stripIndent`\
         ${cmd('{{cmd}}')} could not be issued because this element is currently animating:
@@ -305,7 +312,6 @@ module.exports = {
           - Passing \`{animationDistanceThreshold: 20}\` which decreases the sensitivity`,
       docsUrl: 'https://on.cypress.io/element-is-animating',
     },
-    animation_coords_history_invalid: 'coordsHistory must be at least 2 sets of coords',
     animation_check_failed: 'Not enough coord points provided to calculate distance.',
     center_hidden: {
       message: stripIndent`\