diff --git a/.github/workflows/ci-e2e.yml b/.github/workflows/ci-e2e.yml
index 4ec28981e5f1d..8b556802279a1 100644
--- a/.github/workflows/ci-e2e.yml
+++ b/.github/workflows/ci-e2e.yml
@@ -229,7 +229,6 @@ jobs:
               uses: cypress-io/github-action@v6
               with:
                   config-file: cypress.e2e.config.ts
-                  config: retries=2
                   spec: ${{ matrix.chunk }}
                   install: false
                   # We were seeing suprising crashes in headless mode
diff --git a/cypress.e2e.config.ts b/cypress.e2e.config.ts
index 1b5344ee3bf99..d8023fa4de922 100644
--- a/cypress.e2e.config.ts
+++ b/cypress.e2e.config.ts
@@ -24,8 +24,8 @@ const checkFileDownloaded = async (filename: string, timeout: number, delayMs =
 
 export default defineConfig({
     video: false,
-    defaultCommandTimeout: 20000,
-    requestTimeout: 8000,
+    defaultCommandTimeout: 40000,
+    requestTimeout: 16000,
     pageLoadTimeout: 80000,
     projectId: 'twojfp',
     viewportWidth: 1200,
@@ -34,7 +34,7 @@ export default defineConfig({
     // cypress default is 'top' this means sometimes the element is underneath the top navbar
     // not what a human would do... so, set it to center to avoid this weird behavior
     scrollBehavior: 'center',
-    retries: { runMode: 2 },
+    retries: { runMode: 3 },
     e2e: {
         // We've imported your old cypress plugins here.
         // You may want to clean this up later by importing these.
diff --git a/cypress/e2e/billing.cy.ts b/cypress/e2e/billing.cy.ts
index a32b416abc39e..5b38d8e760d50 100644
--- a/cypress/e2e/billing.cy.ts
+++ b/cypress/e2e/billing.cy.ts
@@ -7,33 +7,39 @@ describe('Billing', () => {
         cy.visit('/organization/billing')
     })
 
-    it('Show and submit unsubscribe survey', () => {
-        cy.intercept('/api/billing/deactivate?products=product_analytics', {
-            fixture: 'api/billing/billing-unsubscribed-product-analytics.json',
-        }).as('unsubscribeProductAnalytics')
+    it(
+        'Show and submit unsubscribe survey',
+        {
+            retries: 4,
+        },
+        () => {
+            cy.intercept('/api/billing/deactivate?products=product_analytics', {
+                fixture: 'api/billing/billing-unsubscribed-product-analytics.json',
+            }).as('unsubscribeProductAnalytics')
 
-        cy.get('[data-attr=more-button]').first().click()
-        cy.contains('.LemonButton', 'Unsubscribe').click()
-        cy.get('.LemonModal h3').should('contain', 'Unsubscribe from Product analytics')
-        cy.get('[data-attr=unsubscribe-reason-too-expensive]').click()
-        cy.get('[data-attr=unsubscribe-reason-survey-textarea]').type('Product analytics')
-        cy.contains('.LemonModal .LemonButton', 'Unsubscribe').click()
-
-        cy.window().then((win) => {
-            const events = (win as any)._cypress_posthog_captures
-            const matchingEvents = events.filter((event) => event.event === 'survey sent')
-            expect(matchingEvents.length).to.equal(1)
-            const matchingEvent = matchingEvents[0]
-            expect(matchingEvent.properties.$survey_id).to.equal(UNSUBSCRIBE_SURVEY_ID)
-            expect(matchingEvent.properties.$survey_response).to.equal('Product analytics')
-            expect(matchingEvent.properties.$survey_response_1).to.equal('product_analytics')
-            expect(matchingEvent.properties.$survey_response_2.length).to.equal(1)
-            expect(matchingEvent.properties.$survey_response_2[0]).to.equal('Too expensive')
-        })
-
-        cy.get('.LemonModal').should('not.exist')
-        cy.wait(['@unsubscribeProductAnalytics'])
-    })
+            cy.get('[data-attr=more-button]').first().click()
+            cy.contains('.LemonButton', 'Unsubscribe').click()
+            cy.get('.LemonModal h3').should('contain', 'Unsubscribe from Product analytics')
+            cy.get('[data-attr=unsubscribe-reason-too-expensive]').click()
+            cy.get('[data-attr=unsubscribe-reason-survey-textarea]').type('Product analytics')
+            cy.contains('.LemonModal .LemonButton', 'Unsubscribe').click()
+
+            cy.window().then((win) => {
+                const events = (win as any)._cypress_posthog_captures
+                const matchingEvents = events.filter((event) => event.event === 'survey sent')
+                expect(matchingEvents.length).to.equal(1)
+                const matchingEvent = matchingEvents[0]
+                expect(matchingEvent.properties.$survey_id).to.equal(UNSUBSCRIBE_SURVEY_ID)
+                expect(matchingEvent.properties.$survey_response).to.equal('Product analytics')
+                expect(matchingEvent.properties.$survey_response_1).to.equal('product_analytics')
+                expect(matchingEvent.properties.$survey_response_2.length).to.equal(1)
+                expect(matchingEvent.properties.$survey_response_2[0]).to.equal('Too expensive')
+            })
+
+            cy.get('.LemonModal').should('not.exist')
+            cy.wait(['@unsubscribeProductAnalytics'])
+        }
+    )
 
     it('Unsubscribe survey text area maintains unique state between product types', () => {
         cy.get('[data-attr=more-button]').first().click()
diff --git a/cypress/e2e/dashboard-deletion.ts b/cypress/e2e/dashboard-deletion.cy.ts
similarity index 100%
rename from cypress/e2e/dashboard-deletion.ts
rename to cypress/e2e/dashboard-deletion.cy.ts
diff --git a/cypress/e2e/dashboard-duplication.ts b/cypress/e2e/dashboard-duplication.cy.ts
similarity index 100%
rename from cypress/e2e/dashboard-duplication.ts
rename to cypress/e2e/dashboard-duplication.cy.ts
diff --git a/cypress/e2e/insights-reload-query.ts b/cypress/e2e/insights-reload-query.cy.ts
similarity index 92%
rename from cypress/e2e/insights-reload-query.ts
rename to cypress/e2e/insights-reload-query.cy.ts
index 55685ae309fb8..134e1146d96c7 100644
--- a/cypress/e2e/insights-reload-query.ts
+++ b/cypress/e2e/insights-reload-query.cy.ts
@@ -5,12 +5,15 @@ describe('ReloadInsight component', () => {
     })
 
     it('saves the query to the URL and localStorage, and reloads it when prompted', () => {
+        cy.intercept('POST', /api\/environments\/\d+\/query\//).as('loadNewQueryInsight')
+
         // Visit the new insight creation page
         cy.visit('/insights/new')
 
         cy.wait(2000)
 
         cy.get('[data-attr="math-selector-0"]').click({ force: true })
+        cy.wait('@loadNewQueryInsight')
         cy.get('[data-attr="math-dau-0"]').click({ force: true })
 
         // Check that the 'draft-query' item is stored in localStorage
diff --git a/cypress/e2e/notebooks-insights.ts b/cypress/e2e/notebooks-insights.cy.ts
similarity index 100%
rename from cypress/e2e/notebooks-insights.ts
rename to cypress/e2e/notebooks-insights.cy.ts