diff --git a/packages/server/modules/workspaces/repositories/workspaceJoinRequests.ts b/packages/server/modules/workspaces/repositories/workspaceJoinRequests.ts
index dac1d1393..c0c1fcf8d 100644
--- a/packages/server/modules/workspaces/repositories/workspaceJoinRequests.ts
+++ b/packages/server/modules/workspaces/repositories/workspaceJoinRequests.ts
@@ -23,7 +23,11 @@ const tables = {
 export const createWorkspaceJoinRequestFactory =
   ({ db }: { db: Knex }): CreateWorkspaceJoinRequest =>
   async ({ workspaceJoinRequest }) => {
-    const res = await tables.workspaceJoinRequests(db).insert(workspaceJoinRequest, '*')
+    const res = await tables
+      .workspaceJoinRequests(db)
+      .insert(workspaceJoinRequest, '*')
+      .onConflict()
+      .ignore()
     return res[0]
   }
 
diff --git a/packages/server/modules/workspaces/services/workspaceJoinRequests.ts b/packages/server/modules/workspaces/services/workspaceJoinRequests.ts
index 1be5235b3..ef6c97b22 100644
--- a/packages/server/modules/workspaces/services/workspaceJoinRequests.ts
+++ b/packages/server/modules/workspaces/services/workspaceJoinRequests.ts
@@ -84,7 +84,7 @@ export const requestToJoinWorkspaceFactory =
       throw new WorkspaceProtectedError()
     }
 
-    await createWorkspaceJoinRequest({
+    const joinRequest = await createWorkspaceJoinRequest({
       workspaceJoinRequest: {
         userId,
         workspaceId,
@@ -92,6 +92,11 @@ export const requestToJoinWorkspaceFactory =
       }
     })
 
+    if (!joinRequest || joinRequest.status !== 'pending') {
+      // The request was already created, so don't send the email again
+      return true
+    }
+
     await sendWorkspaceJoinRequestReceivedEmail({
       workspace,
       requester
diff --git a/packages/server/modules/workspaces/tests/integration/workspaceJoinRequests.spec.ts b/packages/server/modules/workspaces/tests/integration/workspaceJoinRequests.spec.ts
index ada605204..0a936b5b2 100644
--- a/packages/server/modules/workspaces/tests/integration/workspaceJoinRequests.spec.ts
+++ b/packages/server/modules/workspaces/tests/integration/workspaceJoinRequests.spec.ts
@@ -233,6 +233,95 @@ const { FF_WORKSPACES_MODULE_ENABLED } = getFeatureFlags()
         )
         expect(sendWorkspaceJoinRequestReceivedEmailCalls[0].requester).to.equal(user)
       })
+      it('duplicate request is idempotent', async () => {
+        const createWorkspaceJoinRequest = createWorkspaceJoinRequestFactory({ db })
+
+        const sendWorkspaceJoinRequestReceivedEmailCalls: Parameters<SendWorkspaceJoinRequestReceivedEmail>[number][] =
+          []
+        const sendWorkspaceJoinRequestReceivedEmail = async (
+          args: Parameters<SendWorkspaceJoinRequestReceivedEmail>[number]
+        ) => sendWorkspaceJoinRequestReceivedEmailCalls.push(args)
+
+        const user: BasicTestUser = {
+          id: '',
+          name: 'John Speckle',
+          email: `${createRandomString()}@example.org`,
+          role: Roles.Server.Admin,
+          verified: true
+        }
+
+        await createTestUser(user)
+
+        const workspace: BasicTestWorkspace = {
+          id: '',
+          slug: '',
+          ownerId: '',
+          name: cryptoRandomString({ length: 6 }),
+          description: cryptoRandomString({ length: 12 }),
+          discoverabilityEnabled: true
+        }
+        await createTestWorkspace(workspace, user, { domain: 'example.org' })
+        const domain = {
+          id: cryptoRandomString({ length: 10 }),
+          workspaceId: workspace.id,
+          domain: 'example.org',
+          verified: true,
+          createdAt: new Date(),
+          createdByUserId: user.id,
+          updatedAt: new Date()
+        }
+
+        const requestToJoinWorkspace = await requestToJoinWorkspaceFactory({
+          createWorkspaceJoinRequest,
+          sendWorkspaceJoinRequestReceivedEmail:
+            sendWorkspaceJoinRequestReceivedEmail as unknown as SendWorkspaceJoinRequestReceivedEmail,
+          getUserById: async () => user as unknown as UserWithOptionalRole,
+          getWorkspaceWithDomains: async () =>
+            ({
+              ...workspace,
+              domains: [domain]
+            } as unknown as WorkspaceWithDomains),
+          getUserEmails: async () =>
+            [{ email: user.email, verified: true }] as unknown as UserEmail[]
+        })
+
+        expect(
+          await requestToJoinWorkspace({ workspaceId: workspace.id, userId: user.id })
+        ).to.equal(true)
+
+        expect(
+          (await db<WorkspaceJoinRequest>(WorkspaceJoinRequests.name)
+            .where({
+              workspaceId: workspace.id,
+              userId: user.id
+            })
+            .select('status')
+            .first())!.status
+        ).to.equal('pending')
+
+        expect(sendWorkspaceJoinRequestReceivedEmailCalls).to.have.length(1)
+        expect(sendWorkspaceJoinRequestReceivedEmailCalls[0].workspace.id).to.equal(
+          workspace.id
+        )
+        expect(sendWorkspaceJoinRequestReceivedEmailCalls[0].requester).to.equal(user)
+
+        // attempt to join again
+        expect(
+          await requestToJoinWorkspace({ workspaceId: workspace.id, userId: user.id })
+        ).to.equal(true)
+
+        expect(
+          (await db<WorkspaceJoinRequest>(WorkspaceJoinRequests.name)
+            .where({
+              workspaceId: workspace.id,
+              userId: user.id
+            })
+            .select('status')
+            .first())!.status
+        ).to.equal('pending')
+
+        expect(sendWorkspaceJoinRequestReceivedEmailCalls).to.have.length(1)
+      })
     })
 
     describe('approveWorkspaceJoinRequestFactory, returns a function that ', () => {