diff --git a/packages/checkout/src/components/SequenceCheckoutProvider/SequenceCheckoutProvider.tsx b/packages/checkout/src/components/SequenceCheckoutProvider/SequenceCheckoutProvider.tsx
index 10d4c008f..4f1f67e65 100644
--- a/packages/checkout/src/components/SequenceCheckoutProvider/SequenceCheckoutProvider.tsx
+++ b/packages/checkout/src/components/SequenceCheckoutProvider/SequenceCheckoutProvider.tsx
@@ -56,7 +56,9 @@ export type SequenceCheckoutProviderProps = {
 const getDefaultLocationCheckout = (): NavigationCheckout => {
   return {
     location: 'payment-method-selection',
-    params: {}
+    params: {
+      isInitialBalanceChecked: false
+    }
   }
 }
 export const SequenceCheckoutProvider = ({ children, config }: SequenceCheckoutProviderProps) => {
diff --git a/packages/checkout/src/contexts/NavigationCheckout.ts b/packages/checkout/src/contexts/NavigationCheckout.ts
index d9d6d5ba3..0b485d1ec 100644
--- a/packages/checkout/src/contexts/NavigationCheckout.ts
+++ b/packages/checkout/src/contexts/NavigationCheckout.ts
@@ -7,6 +7,7 @@ export interface PaymentMethodSelectionParams {
     address: string
     chainId: number
   }
+  isInitialBalanceChecked: boolean
 }
 
 export interface PaymentMehodSelection {
diff --git a/packages/checkout/src/views/Checkout/PaymentMethodSelect/PayWithCrypto/index.tsx b/packages/checkout/src/views/Checkout/PaymentMethodSelect/PayWithCrypto/index.tsx
index e222175c9..b0deae4ab 100644
--- a/packages/checkout/src/views/Checkout/PaymentMethodSelect/PayWithCrypto/index.tsx
+++ b/packages/checkout/src/views/Checkout/PaymentMethodSelect/PayWithCrypto/index.tsx
@@ -24,11 +24,14 @@ import { useAccount, useChainId, usePublicClient, useReadContract, useSwitchChai
 
 import { ERC_20_CONTRACT_ABI } from '../../../../constants/abi.js'
 import { EVENT_SOURCE } from '../../../../constants/index.js'
+import { type PaymentMethodSelectionParams } from '../../../../contexts/NavigationCheckout.js'
 import type { SelectPaymentSettings } from '../../../../contexts/SelectPaymentModal.js'
 import { useAddFundsModal } from '../../../../hooks/index.js'
 import { useSelectPaymentModal, useTransactionStatusModal } from '../../../../hooks/index.js'
 import { useNavigationCheckout } from '../../../../hooks/useNavigationCheckout.js'
 
+import { useInitialBalanceCheck } from './useInitialBalanceCheck.js'
+
 interface PayWithCryptoTabProps {
   skipOnCloseCallback: () => void
   isSwitchingChainRef: RefObject<boolean>
@@ -156,7 +159,8 @@ export const PayWithCryptoTab = ({ skipOnCloseCallback, isSwitchingChainRef }: P
   const isNotEnoughBalanceError =
     typeof swapQuoteError?.cause === 'string' && swapQuoteError?.cause?.includes('not enough balance for swap')
 
-  const selectedCurrencyPrice = isSwapTransaction ? swapQuote?.maxPrice || 0 : price || 0
+  const maxPrice = swapQuote?.maxPrice && swapQuote.maxPrice !== '' ? swapQuote.maxPrice : 0
+  const selectedCurrencyPrice = isSwapTransaction ? maxPrice : price || 0
 
   const { data: allowanceData, isLoading: allowanceIsLoading } = useReadContract({
     abi: ERC_20_CONTRACT_ABI,
@@ -169,20 +173,33 @@ export const PayWithCryptoTab = ({ skipOnCloseCallback, isSwitchingChainRef }: P
     }
   })
 
+  const isInitialBalanceChecked = (navigation.params as PaymentMethodSelectionParams).isInitialBalanceChecked
+
   const isLoading =
     isLoadingCoinPrice ||
     isLoadingCurrencyInfo ||
     (allowanceIsLoading && !isNativeToken) ||
     isLoadingSwapQuote ||
     tokenBalancesIsLoading ||
-    isLoadingSelectedCurrencyInfo
+    isLoadingSelectedCurrencyInfo ||
+    !isInitialBalanceChecked
 
   const tokenBalance = tokenBalancesData?.pages?.[0]?.balances?.find(balance =>
     compareAddress(balance.contractAddress, selectedCurrency.address)
   )
 
   const isInsufficientBalance =
-    tokenBalance === undefined || (tokenBalance?.balance && BigInt(tokenBalance.balance) < BigInt(selectedCurrencyPrice))
+    tokenBalance === undefined ||
+    (tokenBalance?.balance && tokenBalance.balance !== '' && BigInt(tokenBalance.balance) < BigInt(selectedCurrencyPrice))
+
+  useInitialBalanceCheck({
+    userAddress: userAddress || '',
+    buyCurrencyAddress,
+    price,
+    chainId,
+    isInsufficientBalance: isInsufficientBalance as boolean,
+    tokenBalancesIsLoading
+  })
 
   const isApproved: boolean = (allowanceData as bigint) >= BigInt(price) || isNativeToken
 
diff --git a/packages/checkout/src/views/Checkout/PaymentMethodSelect/PayWithCrypto/useInitialBalanceCheck.tsx b/packages/checkout/src/views/Checkout/PaymentMethodSelect/PayWithCrypto/useInitialBalanceCheck.tsx
new file mode 100644
index 000000000..61a786c8e
--- /dev/null
+++ b/packages/checkout/src/views/Checkout/PaymentMethodSelect/PayWithCrypto/useInitialBalanceCheck.tsx
@@ -0,0 +1,117 @@
+import { compareAddress, ContractVerificationStatus } from '@0xsequence/connect'
+import { useGetSwapRoutes, useGetTokenBalancesSummary } from '@0xsequence/hooks'
+import { useEffect } from 'react'
+import { zeroAddress } from 'viem'
+
+import { type PaymentMethodSelectionParams } from '../../../../contexts/NavigationCheckout.js'
+import { useNavigationCheckout } from '../../../../hooks/useNavigationCheckout.js'
+
+interface UseInitialBalanceCheckArgs {
+  userAddress: string
+  buyCurrencyAddress: string
+  price: string
+  chainId: number
+  isInsufficientBalance: boolean
+  tokenBalancesIsLoading: boolean
+}
+
+// Hook to check if the user has enough of a balance of the
+// initial currency to purchase the item
+// If not, a swap route for which he has enough balance will be selected
+export const useInitialBalanceCheck = ({
+  userAddress,
+  buyCurrencyAddress,
+  price,
+  chainId,
+  isInsufficientBalance,
+  tokenBalancesIsLoading
+}: UseInitialBalanceCheckArgs) => {
+  const { navigation, setNavigation } = useNavigationCheckout()
+
+  const isInitialBalanceChecked = (navigation.params as PaymentMethodSelectionParams).isInitialBalanceChecked
+
+  const { data: swapRoutes = [], isLoading: swapRoutesIsLoading } = useGetSwapRoutes(
+    {
+      walletAddress: userAddress ?? '',
+      toTokenAddress: buyCurrencyAddress,
+      toTokenAmount: price,
+      chainId: chainId
+    },
+    {
+      disabled: isInitialBalanceChecked || !isInsufficientBalance
+    }
+  )
+
+  const { data: swapRoutesTokenBalancesData, isLoading: swapRoutesTokenBalancesIsLoading } = useGetTokenBalancesSummary(
+    {
+      chainIds: [chainId],
+      filter: {
+        accountAddresses: userAddress ? [userAddress] : [],
+        contractStatus: ContractVerificationStatus.ALL,
+        contractWhitelist: swapRoutes
+          .flatMap(route => route.fromTokens)
+          .map(token => token.address)
+          .filter(address => compareAddress(address, zeroAddress)),
+        omitNativeBalances: false
+      },
+      omitMetadata: true
+    },
+    {
+      disabled: isInitialBalanceChecked || !isInsufficientBalance || swapRoutesIsLoading
+    }
+  )
+
+  const findSwapQuote = async () => {
+    let validSwapRoute: string | undefined
+
+    const route = swapRoutes[0]
+    for (let j = 0; j < route.fromTokens.length; j++) {
+      const fromToken = route.fromTokens[j]
+      const balance = swapRoutesTokenBalancesData?.pages?.[0]?.balances?.find(balance =>
+        compareAddress(balance.contractAddress, fromToken.address)
+      )
+
+      if (!balance) {
+        continue
+      }
+      if (BigInt(balance.balance || '0') >= BigInt(fromToken.price || '0')) {
+        validSwapRoute = fromToken.address
+        break
+      }
+    }
+
+    setNavigation({
+      location: 'payment-method-selection',
+      params: {
+        ...navigation.params,
+        selectedCurrency: {
+          address: validSwapRoute || buyCurrencyAddress,
+          chainId: chainId
+        },
+        isInitialBalanceChecked: true
+      }
+    })
+  }
+
+  useEffect(() => {
+    if (!isInitialBalanceChecked && !tokenBalancesIsLoading && !swapRoutesIsLoading && !swapRoutesTokenBalancesIsLoading) {
+      if (isInsufficientBalance) {
+        findSwapQuote()
+      } else {
+        setNavigation({
+          location: 'payment-method-selection',
+          params: {
+            ...navigation.params,
+            isInitialBalanceChecked: true
+          }
+        })
+      }
+    }
+  }, [
+    isInitialBalanceChecked,
+    isInsufficientBalance,
+    tokenBalancesIsLoading,
+    swapRoutesIsLoading,
+    swapRoutesTokenBalancesIsLoading
+  ])
+}
diff --git a/packages/checkout/src/views/Checkout/TokenSelection/index.tsx b/packages/checkout/src/views/Checkout/TokenSelection/index.tsx
index f8dc2984f..ee80a9fab 100644
--- a/packages/checkout/src/views/Checkout/TokenSelection/index.tsx
+++ b/packages/checkout/src/views/Checkout/TokenSelection/index.tsx
@@ -124,7 +124,8 @@ export const TokenSelectionContent = () => {
                       selectedCurrency: {
                         address: token.contractAddress,
                         chainId: token.chainId
-                      }
+                      },
+                      isInitialBalanceChecked: true
                     }
                   }
                 ])