diff --git a/.github/workflows/gradle.yml b/.github/workflows/gradle.yml
index 59a1965d9676..514747f4f491 100644
--- a/.github/workflows/gradle.yml
+++ b/.github/workflows/gradle.yml
@@ -440,6 +440,8 @@ jobs:
         run: SUB_BUILD=PLATFORM ./gradlew --no-daemon assemble --scan
 
       - name: Run End-to-End Frontend Tests
+        env:
+          CYPRESS_WEBAPP_KEY: ${{ secrets.CYPRESS_WEBAPP_KEY }}
         run: ./tools/bin/e2e_test.sh
   # In case of self-hosted EC2 errors, remove this block.
   stop-frontend-test-runner:
diff --git a/airbyte-webapp-e2e-tests/build.gradle b/airbyte-webapp-e2e-tests/build.gradle
index df78f6404cd2..fc10a04ef1ad 100644
--- a/airbyte-webapp-e2e-tests/build.gradle
+++ b/airbyte-webapp-e2e-tests/build.gradle
@@ -13,8 +13,15 @@ node {
 
 task e2etest(type: NpmTask) {
     dependsOn npmInstall
-
-    args = ['run', 'cypress:ci']
+    // If the cypressWebappKey property has been set from the outside (see tools/bin/e2e_test.sh)
+    // we'll record the cypress session, otherwise we're not recording
+    def recordCypress = project.hasProperty('cypressWebappKey') && project.getProperty('cypressWebappKey')
+    if (recordCypress) {
+        environment = [CYPRESS_KEY: project.getProperty('cypressWebappKey')]
+        args = ['run', 'cypress:ci:record']
+    } else {
+        args = ['run', 'cypress:ci']
+    }
     inputs.files fileTree('cypress')
     inputs.file 'package.json'
     inputs.file 'package-lock.json'
diff --git a/airbyte-webapp-e2e-tests/cypress.json b/airbyte-webapp-e2e-tests/cypress.json
index 67b3f620bfcc..cd22f12502da 100644
--- a/airbyte-webapp-e2e-tests/cypress.json
+++ b/airbyte-webapp-e2e-tests/cypress.json
@@ -1,4 +1,5 @@
 {
+  "projectId": "916nvw",
   "baseUrl": "http://localhost:3000",
   "testFiles": [
     "base.spec.js",
diff --git a/airbyte-webapp-e2e-tests/cypress/integration/connection.spec.js b/airbyte-webapp-e2e-tests/cypress/integration/connection.spec.js
index 7c103f46a3bb..29cabfe39485 100644
--- a/airbyte-webapp-e2e-tests/cypress/integration/connection.spec.js
+++ b/airbyte-webapp-e2e-tests/cypress/integration/connection.spec.js
@@ -1,4 +1,8 @@
 describe("Connection main actions", () => {
+  beforeEach(() => {
+    cy.initialSetupCompleted();
+  });
+
   it("Create new connection", () => {
     cy.createTestConnection("Test connection source cypress", "Test destination cypress");
 
@@ -6,7 +10,7 @@ describe("Connection main actions", () => {
     cy.get("div").contains("Test destination cypress").should("exist");
   });
 
-  it.only("Update connection", () => {
+  it("Update connection", () => {
     cy.intercept("/api/v1/web_backend/connections/update").as("updateConnection");
 
     cy.createTestConnection("Test update connection source cypress", "Test update connection destination cypress");
diff --git a/airbyte-webapp-e2e-tests/cypress/integration/destination.spec.js b/airbyte-webapp-e2e-tests/cypress/integration/destination.spec.js
index 8d64a08263d8..94524c9135ac 100644
--- a/airbyte-webapp-e2e-tests/cypress/integration/destination.spec.js
+++ b/airbyte-webapp-e2e-tests/cypress/integration/destination.spec.js
@@ -1,4 +1,8 @@
 describe("Destination main actions", () => {
+  beforeEach(() => {
+    cy.initialSetupCompleted();
+  });
+
   it("Create new destination", () => {
     cy.createTestDestination("Test destination cypress");
 
diff --git a/airbyte-webapp-e2e-tests/cypress/integration/onboarding.spec.js b/airbyte-webapp-e2e-tests/cypress/integration/onboarding.spec.js
index 3a8301160465..b6ad80ceb2b2 100644
--- a/airbyte-webapp-e2e-tests/cypress/integration/onboarding.spec.js
+++ b/airbyte-webapp-e2e-tests/cypress/integration/onboarding.spec.js
@@ -1,4 +1,8 @@
 describe("Preferences actions", () => {
+  beforeEach(() => {
+    cy.initialSetupCompleted(false);
+  });
+
   it("Should redirect to onboarding after email is entered", () => {
     cy.visit("/preferences");
     cy.url().should("include", `/preferences`);
diff --git a/airbyte-webapp-e2e-tests/cypress/integration/source.spec.js b/airbyte-webapp-e2e-tests/cypress/integration/source.spec.js
index 581251d4445c..8b486d47dcf0 100644
--- a/airbyte-webapp-e2e-tests/cypress/integration/source.spec.js
+++ b/airbyte-webapp-e2e-tests/cypress/integration/source.spec.js
@@ -1,4 +1,8 @@
 describe("Source main actions", () => {
+  beforeEach(() => {
+    cy.initialSetupCompleted();
+  });
+
   it("Create new source", () => {
     cy.createTestSource("Test source cypress");
 
diff --git a/airbyte-webapp-e2e-tests/cypress/support/commands/index.ts b/airbyte-webapp-e2e-tests/cypress/support/commands/index.ts
index 3ffc02becb89..281bf7833b84 100644
--- a/airbyte-webapp-e2e-tests/cypress/support/commands/index.ts
+++ b/airbyte-webapp-e2e-tests/cypress/support/commands/index.ts
@@ -3,3 +3,4 @@ import "./sidebar";
 import "./source";
 import "./destination";
 import "./connection";
+import "./workspaces";
diff --git a/airbyte-webapp-e2e-tests/cypress/support/commands/workspaces.js b/airbyte-webapp-e2e-tests/cypress/support/commands/workspaces.js
new file mode 100644
index 000000000000..3111fc247cf2
--- /dev/null
+++ b/airbyte-webapp-e2e-tests/cypress/support/commands/workspaces.js
@@ -0,0 +1,10 @@
+Cypress.Commands.add("initialSetupCompleted", (completed = true) => {
+  // Modify the workspaces/list response to mark every workspace as "initialSetupComplete" to ensure we're not showing
+  // the setup/preference page for any workspace if this method got called.
+  cy.intercept("POST", "/api/v1/workspaces/list", (req) => {
+    req.continue(res => {
+      res.body.workspaces = res.body.workspaces.map(ws => ({ ...ws, initialSetupComplete: completed }));
+      res.send(res.body);
+    });
+  });
+});
diff --git a/airbyte-webapp-e2e-tests/package.json b/airbyte-webapp-e2e-tests/package.json
index 25eff6858bff..09a50a2b076b 100644
--- a/airbyte-webapp-e2e-tests/package.json
+++ b/airbyte-webapp-e2e-tests/package.json
@@ -4,7 +4,8 @@
   "description": "Airbyte e2e testing",
   "scripts": {
     "cypress:open": "cypress open",
-    "cypress:ci": "CYPRESS_BASE_URL=http://localhost:8000 cypress run"
+    "cypress:ci": "CYPRESS_BASE_URL=http://localhost:8000 cypress run",
+    "cypress:ci:record": "CYPRESS_BASE_URL=http://localhost:8000 cypress run --record --key $CYPRESS_KEY"
   },
   "eslintConfig": {
     "env": {
diff --git a/tools/bin/e2e_test.sh b/tools/bin/e2e_test.sh
index 7deb9bdf2437..e0e194e6eff3 100755
--- a/tools/bin/e2e_test.sh
+++ b/tools/bin/e2e_test.sh
@@ -16,11 +16,15 @@ mkdir -p /tmp/airbyte_local
 
 # Detach so we can run subsequent commands
 VERSION=dev TRACKING_STRATEGY=logging docker-compose up -d
-trap 'echo "docker-compose logs:" && docker-compose logs -t --tail 1000 && docker-compose down && docker rm -f $(docker ps -q --filter name=airbyte_ci_pg)' EXIT
+trap 'echo "docker-compose logs:" && docker-compose logs -t --tail 1000 && docker-compose down && docker stop airbyte_ci_pg' EXIT
 
-docker run -d -p 5433:5432 -e POSTGRES_PASSWORD=secret_password -e POSTGRES_DB=airbyte_ci --name airbyte_ci_pg postgres
-echo "Waiting for services to begin"
-sleep 30 # TODO need a better way to wait
+docker run --rm -d -p 5433:5432 -e POSTGRES_PASSWORD=secret_password -e POSTGRES_DB=airbyte_ci --name airbyte_ci_pg postgres
+echo "Waiting for health API to be available..."
+# Retry loading the health API of the server to check that the server is fully available
+until $(curl --output /dev/null --fail --silent --max-time 5 --head localhost:8001/api/v1/health); do
+  echo "Health API not available yet. Retrying in 10 seconds..."
+  sleep 10
+done
 
 echo "Running e2e tests via gradle"
-SUB_BUILD=PLATFORM ./gradlew --no-daemon :airbyte-webapp-e2e-tests:e2etest
+SUB_BUILD=PLATFORM ./gradlew --no-daemon :airbyte-webapp-e2e-tests:e2etest -PcypressWebappKey=$CYPRESS_WEBAPP_KEY