diff --git a/apps/web/playwright/booking-pages.e2e.ts b/apps/web/playwright/booking-pages.e2e.ts
index 4a6a934e8d..c5637246d5 100644
--- a/apps/web/playwright/booking-pages.e2e.ts
+++ b/apps/web/playwright/booking-pages.e2e.ts
@@ -75,6 +75,26 @@ test.describe("user with a special character in the username", () => {
     const response = await page.goto(`/${user.username}/30-min`);
     expect(response?.status()).not.toBe(404);
   });
+
+  test("Should not throw 500 when redirecting user to his/her only event-type page even if username contains special characters", async ({
+    page,
+    users,
+  }) => {
+    const benny = await users.create({
+      username: "ßenny", // ß is a special character
+      eventTypes: [
+        {
+          title: "15 min",
+          slug: "15-min",
+          length: 15,
+        },
+      ],
+      overrideDefaultEventTypes: true,
+    });
+    // This redirects to /[user]/[type] because this user has only 1 event-type
+    const response = await page.goto(`/${benny.username}`);
+    expect(response?.status()).not.toBe(500);
+  });
 });
 
 test.describe("free user", () => {
diff --git a/apps/web/playwright/dynamic-booking-pages.e2e.ts b/apps/web/playwright/dynamic-booking-pages.e2e.ts
index 137e7b4a1f..d67df43f6a 100644
--- a/apps/web/playwright/dynamic-booking-pages.e2e.ts
+++ b/apps/web/playwright/dynamic-booking-pages.e2e.ts
@@ -143,4 +143,33 @@ test.describe("Organization:", () => {
       }
     );
   });
+
+  test("dynamic booking for usernames with special characters", async ({ page, users, orgs }) => {
+    const org = await orgs.create({
+      name: "TestOrg",
+    });
+
+    const user1 = await users.create({
+      organizationId: org.id,
+      name: "User 1",
+      roleInOrganization: MembershipRole.MEMBER,
+    });
+
+    const user2 = await users.create({
+      username: "ßenny-Joo", // ß is a special character
+      organizationId: org.id,
+      name: "User 2",
+      roleInOrganization: MembershipRole.MEMBER,
+    });
+    await doOnOrgDomain(
+      {
+        orgSlug: org.slug,
+        page,
+      },
+      async () => {
+        const response = await page.goto(`/${user1.username}+${user2.username}`);
+        expect(response?.status()).not.toBe(500);
+      }
+    );
+  });
 });
diff --git a/apps/web/playwright/fixtures/users.ts b/apps/web/playwright/fixtures/users.ts
index a57d38e7cf..858b55da09 100644
--- a/apps/web/playwright/fixtures/users.ts
+++ b/apps/web/playwright/fixtures/users.ts
@@ -268,6 +268,7 @@ export const createUsersFixture = (
       opts?:
         | (CustomUserOpts & {
             organizationId?: number | null;
+            overrideDefaultEventTypes?: boolean;
           })
         | null,
       scenario: {
@@ -300,18 +301,20 @@ export const createUsersFixture = (
         },
       });
 
-      let defaultEventTypes: SupportedTestEventTypes[] = [
-        { title: "30 min", slug: "30-min", length: 30 },
-        { title: "Paid", slug: "paid", length: 30, price: 1000 },
-        { title: "Opt in", slug: "opt-in", requiresConfirmation: true, length: 30 },
-        { title: "Seated", slug: "seated", seatsPerTimeSlot: 2, length: 30 },
-        {
-          title: "Multiple duration",
-          slug: "multiple-duration",
-          length: 30,
-          metadata: { multipleDuration: [30, 60, 90] },
-        },
-      ];
+      let defaultEventTypes: SupportedTestEventTypes[] = opts?.overrideDefaultEventTypes
+        ? []
+        : [
+            { title: "30 min", slug: "30-min", length: 30 },
+            { title: "Paid", slug: "paid", length: 30, price: 1000 },
+            { title: "Opt in", slug: "opt-in", requiresConfirmation: true, length: 30 },
+            { title: "Seated", slug: "seated", seatsPerTimeSlot: 2, length: 30 },
+            {
+              title: "Multiple duration",
+              slug: "multiple-duration",
+              length: 30,
+              metadata: { multipleDuration: [30, 60, 90] },
+            },
+          ];
 
       if (opts?.eventTypes) defaultEventTypes = defaultEventTypes.concat(opts.eventTypes);
       for (const eventTypeData of defaultEventTypes) {
diff --git a/apps/web/server/lib/[user]/getServerSideProps.ts b/apps/web/server/lib/[user]/getServerSideProps.ts
index d59545fb01..9dfd12a818 100644
--- a/apps/web/server/lib/[user]/getServerSideProps.ts
+++ b/apps/web/server/lib/[user]/getServerSideProps.ts
@@ -106,7 +106,7 @@ export const getServerSideProps: GetServerSideProps<UserPageProps> = async (cont
   log.debug(safeStringify({ usersInOrgContext, isValidOrgDomain, currentOrgDomain, isDynamicGroup }));
 
   if (isDynamicGroup) {
-    const destinationUrl = `/${usernameList.join("+")}/dynamic`;
+    const destinationUrl = encodeURI(`/${usernameList.join("+")}/dynamic`);
 
     // EXAMPLE - context.params: { orgSlug: 'acme', user: 'member0+owner1' }
     // EXAMPLE - context.query: { redirect: 'undefined', orgRedirection: 'undefined', user: 'member0+owner1' }
@@ -166,7 +166,7 @@ export const getServerSideProps: GetServerSideProps<UserPageProps> = async (cont
     return {
       redirect: {
         permanent: false,
-        destination: `${urlDestination}?${urlQuery}`,
+        destination: `${encodeURI(urlDestination)}?${urlQuery}`,
       },
     };
   }