diff --git a/packages/frontend-2/components/pricingTable/Plan.vue b/packages/frontend-2/components/pricingTable/Plan.vue
index a1d090349..e8a1774bf 100644
--- a/packages/frontend-2/components/pricingTable/Plan.vue
+++ b/packages/frontend-2/components/pricingTable/Plan.vue
@@ -5,8 +5,7 @@
     <div class="lg:h-32">
       <div class="flex items-center gap-x-2">
         <h4 class="text-body font-medium">
-          Workspace
-          <span class="capitalize">{{ plan }}</span>
+          {{ formatName(plan) }}
         </h4>
         <CommonBadge v-if="badgeText" rounded>
           {{ badgeText }}
@@ -92,10 +91,9 @@ import {
   WorkspacePlanStatuses,
   BillingInterval
 } from '~/lib/common/generated/gql/graphql'
-import { startCase } from 'lodash'
 import { XMarkIcon } from '@heroicons/vue/24/outline'
 import { useWorkspacePlanPrices } from '~/lib/billing/composables/prices'
-import { formatPrice } from '~/lib/billing/helpers/prices'
+import { formatPrice, formatName } from '~/lib/billing/helpers/plan'
 import { useBillingActions } from '~/lib/billing/composables/actions'
 
 defineEmits<{
@@ -108,11 +106,12 @@ const props = defineProps<{
   currentPlan: MaybeNullOrUndefined<WorkspacePlan>
   isAdmin: boolean
   activeBillingInterval: MaybeNullOrUndefined<BillingInterval>
+  hasSubscription: boolean
   workspaceId: MaybeNullOrUndefined<string>
 }>()
 
 const { pricesNew } = useWorkspacePlanPrices()
-const { upgradePlan } = useBillingActions()
+const { upgradePlan, redirectToCheckout } = useBillingActions()
 
 const isYearlyIntervalSelected = ref(props.yearlyIntervalSelected)
 
@@ -204,19 +203,20 @@ const isSelectable = computed(() => {
 })
 
 const buttonColor = computed(() => {
-  if (props.currentPlan?.status === WorkspacePlanStatuses.Expired) {
-    return props.plan === WorkspacePlans.Starter ? 'primary' : 'outline'
+  if (props.currentPlan?.name === WorkspacePlans.Free) {
+    return props.plan === WorkspacePlans.Pro ? 'primary' : 'outline'
   }
   return 'outline'
 })
 
 const buttonText = computed(() => {
-  // Allow selection during trial, expired or canceled state
+  // Allow if current plan is Free, or the current plan is expired/canceled
   if (
+    props.currentPlan?.name === WorkspacePlans.Free ||
     props.currentPlan?.status === WorkspacePlanStatuses.Expired ||
     props.currentPlan?.status === WorkspacePlanStatuses.Canceled
   ) {
-    return `Subscribe to ${startCase(props.plan)}`
+    return `Subscribe to ${formatName(props.plan)}`
   }
   // Current plan case
   if (isCurrentPlan.value) {
@@ -234,7 +234,7 @@ const buttonText = computed(() => {
     return 'Change to annual plan'
   }
   // Upgrade case
-  return canUpgradeToPlan.value ? `Upgrade to ${startCase(props.plan)}` : ''
+  return canUpgradeToPlan.value ? `Upgrade to ${formatName(props.plan)}` : ''
 })
 
 const badgeText = computed(() =>
@@ -243,7 +243,9 @@ const badgeText = computed(() =>
 
 const handleUpgradeClick = () => {
   if (!props.workspaceId) return
-  if (props.plan === WorkspacePlans.Team || props.plan === WorkspacePlans.Pro) {
+  if (props.plan !== WorkspacePlans.Team && props.plan !== WorkspacePlans.Pro) return
+
+  if (props.hasSubscription) {
     upgradePlan({
       plan: props.plan,
       cycle: isYearlyIntervalSelected.value
@@ -251,6 +253,14 @@ const handleUpgradeClick = () => {
         : BillingInterval.Monthly,
       workspaceId: props.workspaceId
     })
+  } else {
+    redirectToCheckout({
+      plan: props.plan,
+      cycle: isYearlyIntervalSelected.value
+        ? BillingInterval.Yearly
+        : BillingInterval.Monthly,
+      workspaceId: props.workspaceId
+    })
   }
 }
 
diff --git a/packages/frontend-2/components/pricingTable/PricingTable.vue b/packages/frontend-2/components/pricingTable/PricingTable.vue
index 3a80c33ff..ff0131aca 100644
--- a/packages/frontend-2/components/pricingTable/PricingTable.vue
+++ b/packages/frontend-2/components/pricingTable/PricingTable.vue
@@ -9,6 +9,7 @@
       :active-billing-interval="billingInterval"
       :is-admin="isAdmin"
       :workspace-id="props.workspaceId"
+      :has-subscription="!!subscription"
       @on-yearly-interval-selected="onYearlyIntervalSelected"
     />
   </div>
@@ -34,7 +35,11 @@ const props = defineProps<{
   workspaceId: MaybeNullOrUndefined<string>
 }>()
 
-const { billingInterval, plan: currentPlan } = useWorkspacePlan(props.slug)
+const {
+  billingInterval,
+  plan: currentPlan,
+  subscription
+} = useWorkspacePlan(props.slug)
 
 const isYearlySelected = ref(false)
 
diff --git a/packages/frontend-2/components/settings/workspaces/billing/Page.vue b/packages/frontend-2/components/settings/workspaces/billing/Page.vue
index 8643e9bbb..0d992f3a8 100644
--- a/packages/frontend-2/components/settings/workspaces/billing/Page.vue
+++ b/packages/frontend-2/components/settings/workspaces/billing/Page.vue
@@ -229,7 +229,7 @@ import { useMixpanel } from '~/lib/core/composables/mp'
 import { guideBillingUrl } from '~/lib/common/helpers/route'
 import { adminUpdateWorkspacePlanMutation } from '~/lib/billing/graphql/mutations'
 import { useWorkspacePlanPrices } from '~/lib/billing/composables/prices'
-import { formatPrice } from '~/lib/billing/helpers/prices'
+import { formatPrice } from '~/lib/billing/helpers/plan'
 
 graphql(`
   fragment SettingsWorkspacesBilling_Workspace on Workspace {
diff --git a/packages/frontend-2/components/settings/workspaces/billing/PricingTable/Plan.vue b/packages/frontend-2/components/settings/workspaces/billing/PricingTable/Plan.vue
index dd7c9f56f..d14a9ed83 100644
--- a/packages/frontend-2/components/settings/workspaces/billing/PricingTable/Plan.vue
+++ b/packages/frontend-2/components/settings/workspaces/billing/PricingTable/Plan.vue
@@ -120,7 +120,7 @@ import { startCase, isFunction } from 'lodash'
 import { XMarkIcon } from '@heroicons/vue/24/outline'
 import type { SetupContext } from 'vue'
 import { useWorkspacePlanPrices } from '~/lib/billing/composables/prices'
-import { formatPrice } from '~/lib/billing/helpers/prices'
+import { formatPrice } from '~/lib/billing/helpers/plan'
 
 const emit = defineEmits<{
   (e: 'onYearlyIntervalSelected', value: boolean): void
diff --git a/packages/frontend-2/components/settings/workspaces/billing/Summary.vue b/packages/frontend-2/components/settings/workspaces/billing/Summary.vue
index ad3f1b9b8..89955aaf3 100644
--- a/packages/frontend-2/components/settings/workspaces/billing/Summary.vue
+++ b/packages/frontend-2/components/settings/workspaces/billing/Summary.vue
@@ -7,7 +7,7 @@
       <div class="p-5 pt-4 flex flex-col">
         <h3 class="text-body-xs text-foreground-2 pb-4">Current plan</h3>
         <p class="text-heading-lg text-foreground capitalize">
-          {{ plan?.name }}
+          {{ formatName(plan?.name) }}
         </p>
       </div>
 
@@ -62,6 +62,7 @@
 import { useWorkspacePlan } from '~~/lib/workspaces/composables/plan'
 import { useBillingActions } from '~/lib/billing/composables/actions'
 import type { MaybeNullOrUndefined } from '@speckle/shared'
+import { formatName } from '~/lib/billing/helpers/plan'
 
 defineProps<{
   workspaceId?: MaybeNullOrUndefined<string>
diff --git a/packages/frontend-2/components/settings/workspaces/billing/UpgradeDialog.vue b/packages/frontend-2/components/settings/workspaces/billing/UpgradeDialog.vue
index 58647bf8c..b51575834 100644
--- a/packages/frontend-2/components/settings/workspaces/billing/UpgradeDialog.vue
+++ b/packages/frontend-2/components/settings/workspaces/billing/UpgradeDialog.vue
@@ -31,7 +31,7 @@ import type { PaidWorkspacePlansOld } from '@speckle/shared'
 import { Roles } from '@speckle/shared'
 import { isPaidPlan } from '~/lib/billing/helpers/types'
 import { useWorkspacePlanPrices } from '~/lib/billing/composables/prices'
-import { formatPrice } from '~/lib/billing/helpers/prices'
+import { formatPrice } from '~/lib/billing/helpers/plan'
 
 const props = defineProps<{
   plan: PaidWorkspacePlansOld
diff --git a/packages/frontend-2/lib/billing/helpers/plan.ts b/packages/frontend-2/lib/billing/helpers/plan.ts
new file mode 100644
index 000000000..404a43689
--- /dev/null
+++ b/packages/frontend-2/lib/billing/helpers/plan.ts
@@ -0,0 +1,29 @@
+import { isInteger } from 'lodash-es'
+import { WorkspacePlans } from '@speckle/shared'
+
+export const formatPrice = (price?: { amount: number; currencySymbol: string }) => {
+  if (!price) return ''
+  return `${price.currencySymbol}${
+    isInteger(price.amount) ? price.amount : price.amount.toFixed(2)
+  }`
+}
+
+// Internal plan names dont match the names we use in the product
+export const formatName = (plan?: WorkspacePlans) => {
+  if (!plan) return ''
+
+  const formattedPlanNames: Record<WorkspacePlans, string> = {
+    [WorkspacePlans.Unlimited]: 'Unlimited',
+    [WorkspacePlans.Academia]: 'Academia',
+    [WorkspacePlans.StarterInvoiced]: 'Starter (invoiced)',
+    [WorkspacePlans.PlusInvoiced]: 'Plus (Invoiced)',
+    [WorkspacePlans.BusinessInvoiced]: 'Business (Invoiced)',
+    [WorkspacePlans.Starter]: 'Starter',
+    [WorkspacePlans.Plus]: 'Plus',
+    [WorkspacePlans.Business]: 'Business',
+    [WorkspacePlans.Free]: 'Free',
+    [WorkspacePlans.Team]: 'Starter',
+    [WorkspacePlans.Pro]: 'Business'
+  }
+  return formattedPlanNames[plan]
+}
diff --git a/packages/frontend-2/lib/billing/helpers/prices.ts b/packages/frontend-2/lib/billing/helpers/prices.ts
deleted file mode 100644
index 961d2efe6..000000000
--- a/packages/frontend-2/lib/billing/helpers/prices.ts
+++ /dev/null
@@ -1,8 +0,0 @@
-import { isInteger } from 'lodash-es'
-
-export const formatPrice = (price?: { amount: number; currencySymbol: string }) => {
-  if (!price) return ''
-  return `${price.currencySymbol}${
-    isInteger(price.amount) ? price.amount : price.amount.toFixed(2)
-  }`
-}
diff --git a/packages/frontend-2/lib/workspaces/composables/plan.ts b/packages/frontend-2/lib/workspaces/composables/plan.ts
index a54460a0d..993848a9d 100644
--- a/packages/frontend-2/lib/workspaces/composables/plan.ts
+++ b/packages/frontend-2/lib/workspaces/composables/plan.ts
@@ -78,7 +78,6 @@ export const useWorkspacePlan = (slug: string) => {
   const intervalIsYearly = computed(
     () => billingInterval.value === BillingInterval.Yearly
   )
-
   // TODO: Replace with value from API call, this a placeholder value
   const seatPrice = 15
 
@@ -109,6 +108,7 @@ export const useWorkspacePlan = (slug: string) => {
     billingInterval,
     intervalIsYearly,
     totalCostFormatted,
-    statusIsCancelationScheduled
+    statusIsCancelationScheduled,
+    subscription
   }
 }
diff --git a/packages/shared/src/workspaces/helpers/plans.ts b/packages/shared/src/workspaces/helpers/plans.ts
index 1e5050751..481f0c40f 100644
--- a/packages/shared/src/workspaces/helpers/plans.ts
+++ b/packages/shared/src/workspaces/helpers/plans.ts
@@ -38,12 +38,12 @@ export type PaidWorkspacePlans =
 
 export const UnpaidWorkspacePlans = <const>{
   // Old
-  Unlimited: 'unlimited',
-  Academia: 'academia',
   StarterInvoiced: 'starterInvoiced',
   PlusInvoiced: 'plusInvoiced',
   BusinessInvoiced: 'businessInvoiced',
   // New
+  Unlimited: 'unlimited',
+  Academia: 'academia',
   Free: 'free'
 }