diff --git a/app/src/main/kotlin/com/x8bit/bitwarden/ui/platform/feature/premium/plan/PlanScreen.kt b/app/src/main/kotlin/com/x8bit/bitwarden/ui/platform/feature/premium/plan/PlanScreen.kt
index 20946f07d6..d80f6a60a4 100644
--- a/app/src/main/kotlin/com/x8bit/bitwarden/ui/platform/feature/premium/plan/PlanScreen.kt
+++ b/app/src/main/kotlin/com/x8bit/bitwarden/ui/platform/feature/premium/plan/PlanScreen.kt
@@ -269,6 +269,7 @@ private fun FreeCloudContent(
     handlers: PlanHandlers,
     modifier: Modifier = Modifier,
 ) {
+    var shouldShowUpgradeDialog by rememberSaveable { mutableStateOf(false) }
     Column(
         modifier = modifier
             .fillMaxSize()
@@ -285,7 +286,7 @@ private fun FreeCloudContent(
 
         BitwardenFilledButton(
             label = stringResource(id = BitwardenString.upgrade_now),
-            onClick = handlers.onUpgradeNowClick,
+            onClick = { shouldShowUpgradeDialog = true },
             icon = rememberVectorPainter(id = BitwardenDrawable.ic_external_link),
             modifier = Modifier
                 .standardHorizontalMargin()
@@ -296,7 +297,10 @@ private fun FreeCloudContent(
         Spacer(modifier = Modifier.height(12.dp))
 
         Text(
-            text = stringResource(id = BitwardenString.stripe_checkout_footer),
+            text = stringResource(
+                id = BitwardenString
+                    .youll_go_to_stripes_secure_checkout_to_complete_your_purchase,
+            ),
             style = BitwardenTheme.typography.bodyMedium,
             color = BitwardenTheme.colorScheme.text.secondary,
             textAlign = TextAlign.Center,
@@ -309,6 +313,24 @@ private fun FreeCloudContent(
         Spacer(modifier = Modifier.height(16.dp))
         Spacer(modifier = Modifier.navigationBarsPadding())
     }
+
+    if (shouldShowUpgradeDialog) {
+        BitwardenTwoButtonDialog(
+            title = stringResource(id = BitwardenString.continue_to_stripe),
+            message = stringResource(
+                id = BitwardenString
+                    .youll_go_to_stripes_secure_checkout_to_complete_your_purchase,
+            ),
+            confirmButtonText = stringResource(id = BitwardenString.continue_text),
+            dismissButtonText = stringResource(id = BitwardenString.cancel),
+            onConfirmClick = {
+                shouldShowUpgradeDialog = false
+                handlers.onUpgradeNowClick()
+            },
+            onDismissClick = { shouldShowUpgradeDialog = false },
+            onDismissRequest = { shouldShowUpgradeDialog = false },
+        )
+    }
 }
 
 @Suppress("MaxLineLength")
diff --git a/app/src/test/kotlin/com/x8bit/bitwarden/ui/platform/feature/premium/plan/PlanScreenTest.kt b/app/src/test/kotlin/com/x8bit/bitwarden/ui/platform/feature/premium/plan/PlanScreenTest.kt
index 7bf9127644..c3ba27512b 100644
--- a/app/src/test/kotlin/com/x8bit/bitwarden/ui/platform/feature/premium/plan/PlanScreenTest.kt
+++ b/app/src/test/kotlin/com/x8bit/bitwarden/ui/platform/feature/premium/plan/PlanScreenTest.kt
@@ -136,14 +136,66 @@ class PlanScreenTest : BitwardenComposeTest() {
     }
 
     @Test
-    fun `upgrade now button click should send UpgradeNowClick action`() {
+    fun `upgrade now button click should show continue to Stripe confirmation dialog`() {
+        composeTestRule
+            .onAllNodesWithText("Continue to Stripe?")
+            .filterToOne(hasAnyAncestor(isDialog()))
+            .assertDoesNotExist()
+
         composeTestRule
             .onNodeWithTag("UpgradeNowButton")
             .performScrollTo()
             .performClick()
-        verify {
-            viewModel.trySendAction(PlanAction.UpgradeNowClick)
-        }
+
+        composeTestRule
+            .onAllNodesWithText("Continue to Stripe?")
+            .filterToOne(hasAnyAncestor(isDialog()))
+            .assertExists()
+        composeTestRule
+            .onAllNodesWithText(
+                "You’ll go to Stripe’s secure checkout to complete your purchase.",
+            )
+            .filterToOne(hasAnyAncestor(isDialog()))
+            .assertExists()
+        verify(exactly = 0) { viewModel.trySendAction(PlanAction.UpgradeNowClick) }
+    }
+
+    @Test
+    fun `upgrade now dialog continue click should send UpgradeNowClick action and dismiss`() {
+        composeTestRule
+            .onNodeWithTag("UpgradeNowButton")
+            .performScrollTo()
+            .performClick()
+
+        composeTestRule
+            .onAllNodesWithText("Continue")
+            .filterToOne(hasAnyAncestor(isDialog()))
+            .performClick()
+
+        verify { viewModel.trySendAction(PlanAction.UpgradeNowClick) }
+        composeTestRule
+            .onAllNodesWithText("Continue to Stripe?")
+            .filterToOne(hasAnyAncestor(isDialog()))
+            .assertDoesNotExist()
+    }
+
+    @Test
+    fun `upgrade now dialog cancel click should dismiss without sending action`() {
+        composeTestRule
+            .onNodeWithTag("UpgradeNowButton")
+            .performScrollTo()
+            .performClick()
+
+        composeTestRule
+            .onAllNodesWithText("Cancel")
+            .filterToOne(hasAnyAncestor(isDialog()))
+            .performClick()
+
+        verify(exactly = 0) { viewModel.trySendAction(PlanAction.UpgradeNowClick) }
+        composeTestRule
+            .onAllNodesWithText("Continue to Stripe?")
+            .filterToOne(hasAnyAncestor(isDialog()))
+            .assertDoesNotExist()
     }
 
     @Test
diff --git a/ui/src/main/res/values/strings.xml b/ui/src/main/res/values/strings.xml
index 3baca079ce..83bd98b565 100644
--- a/ui/src/main/res/values/strings.xml
+++ b/ui/src/main/res/values/strings.xml
@@ -1278,7 +1278,7 @@ Do you want to switch to this account?</string>
     <string name="secure_file_storage">Secure file storage</string>
     <string name="breach_monitoring">Breach monitoring</string>
     <string name="upgrade_now">Upgrade now</string>
-    <string name="stripe_checkout_footer">You’ll go to Stripe’s secure checkout to complete your purchase.</string>
+    <string name="youll_go_to_stripes_secure_checkout_to_complete_your_purchase">You’ll go to Stripe’s secure checkout to complete your purchase.</string>
     <string name="opening_checkout">Opening checkout…</string>
     <string name="secure_checkout_didnt_load">Secure checkout didn’t load</string>
     <string name="trouble_opening_payment_page">We had trouble opening the payment page, so try again.</string>