diff --git a/apps/cowswap-frontend/src/legacy/state/price/hooks.ts b/apps/cowswap-frontend/src/legacy/state/price/hooks.ts
index 798c0e7bd9..b6f4ee84e6 100644
--- a/apps/cowswap-frontend/src/legacy/state/price/hooks.ts
+++ b/apps/cowswap-frontend/src/legacy/state/price/hooks.ts
@@ -5,15 +5,15 @@ import { SupportedChainId as ChainId } from '@cowprotocol/cow-sdk'
 import { useDispatch, useSelector } from 'react-redux'
 
 import {
-  updateQuote,
-  UpdateQuoteParams,
   ClearQuoteParams,
   getNewQuote,
   GetQuoteParams,
   refreshQuote,
-  SetQuoteErrorParams,
-  setQuoteError,
   RefreshQuoteParams,
+  setQuoteError,
+  SetQuoteErrorParams,
+  updateQuote,
+  UpdateQuoteParams,
 } from './actions'
 import { QuoteInformationObject, QuotesMap } from './reducer'
 
diff --git a/apps/cowswap-frontend/src/legacy/state/swap/TradeGp.ts b/apps/cowswap-frontend/src/legacy/state/swap/TradeGp.ts
index d98caa57cd..6f80a40406 100644
--- a/apps/cowswap-frontend/src/legacy/state/swap/TradeGp.ts
+++ b/apps/cowswap-frontend/src/legacy/state/swap/TradeGp.ts
@@ -13,7 +13,7 @@ interface FeeInformation {
   amount: string
 }
 
-export type FeeForTrade = { feeAsCurrency: CurrencyAmount<Currency> } & Pick<FeeInformation, 'amount'>
+export type FeeForTrade = { feeAsCurrency: CurrencyAmount<Currency> } & FeeInformation
 
 type TradeExecutionPrice = CanonicalMarketParams<CurrencyAmount<Currency> | undefined> & { price?: PriceInformation }
 
diff --git a/apps/cowswap-frontend/src/modules/swap/helpers/getSwapButtonState.ts b/apps/cowswap-frontend/src/modules/swap/helpers/getSwapButtonState.ts
index f1ef7b1ee6..5404004120 100644
--- a/apps/cowswap-frontend/src/modules/swap/helpers/getSwapButtonState.ts
+++ b/apps/cowswap-frontend/src/modules/swap/helpers/getSwapButtonState.ts
@@ -1,9 +1,11 @@
 import { Token } from '@uniswap/sdk-core'
 
 import { QuoteError } from 'legacy/state/price/actions'
+import { QuoteInformationObject } from 'legacy/state/price/reducer'
 import TradeGp from 'legacy/state/swap/TradeGp'
 
 import { getEthFlowEnabled } from 'modules/swap/helpers/getEthFlowEnabled'
+import { isQuoteExpired } from 'modules/tradeQuote/utils/isQuoteExpired'
 
 import { ApprovalState } from 'common/hooks/useApproveState'
 
@@ -18,6 +20,7 @@ export enum SwapButtonState {
   TransferToSmartContract = 'TransferToSmartContract',
   UnsupportedToken = 'UnsupportedToken',
   FetchQuoteError = 'FetchQuoteError',
+  QuoteExpired = 'QuoteExpired',
   OfflineBrowser = 'OfflineBrowser',
   Loading = 'Loading',
   WalletIsNotConnected = 'WalletIsNotConnected',
@@ -39,7 +42,7 @@ export interface SwapButtonStateParams {
   isReadonlyGnosisSafeUser: boolean
   isSwapUnsupported: boolean
   isBundlingSupported: boolean
-  quoteError: QuoteError | undefined | null
+  quote: QuoteInformationObject | undefined | null
   inputError?: string
   approvalState: ApprovalState
   feeWarningAccepted: boolean
@@ -66,7 +69,8 @@ const quoteErrorToSwapButtonState: { [key in QuoteError]: SwapButtonState | null
 }
 
 export function getSwapButtonState(input: SwapButtonStateParams): SwapButtonState {
-  const { quoteError, approvalState, isPermitSupported, amountsForSignature } = input
+  const { quote, approvalState, isPermitSupported, amountsForSignature } = input
+  const quoteError = quote?.error
 
   // show approve flow when: no error on inputs, not approved or pending, or approved in current session
   // never show if price impact is above threshold
@@ -104,6 +108,10 @@ export function getSwapButtonState(input: SwapButtonStateParams): SwapButtonStat
     return SwapButtonState.ReadonlyGnosisSafeUser
   }
 
+  if (isQuoteExpired(quote?.fee?.expirationDate) === true) {
+    return SwapButtonState.QuoteExpired
+  }
+
   if (!input.isNativeIn && showApproveFlow) {
     if (input.isBundlingSupported) {
       return SwapButtonState.ApproveAndSwap
diff --git a/apps/cowswap-frontend/src/modules/swap/hooks/useFlowContext.ts b/apps/cowswap-frontend/src/modules/swap/hooks/useFlowContext.ts
index da502128cb..482e725397 100644
--- a/apps/cowswap-frontend/src/modules/swap/hooks/useFlowContext.ts
+++ b/apps/cowswap-frontend/src/modules/swap/hooks/useFlowContext.ts
@@ -89,7 +89,7 @@ export function useBaseFlowContextSetup(): BaseFlowContextSetup {
   const { allowsOffchainSigning } = useWalletDetails()
   const gnosisSafeInfo = useGnosisSafeInfo()
   const { recipient } = useSwapState()
-  const { v2Trade: trade } = useDerivedSwapInfo()
+  const { v2Trade: trade, allowedSlippage } = useDerivedSwapInfo()
   const swapZeroFee = useSwapZeroFee()
 
   const appData = useAppData()
@@ -107,7 +107,6 @@ export function useBaseFlowContextSetup(): BaseFlowContextSetup {
   const isSafeEthFlow = useIsSafeEthFlow()
   const getCachedPermit = useGetCachedPermit()
 
-  const { allowedSlippage } = useDerivedSwapInfo()
   const [inputAmountWithSlippage, outputAmountWithSlippage] = useSwapAmountsWithSlippage()
   const sellTokenContract = useTokenContract(getAddress(inputAmountWithSlippage?.currency) || undefined, true)
 
diff --git a/apps/cowswap-frontend/src/modules/swap/hooks/useSwapButtonContext.ts b/apps/cowswap-frontend/src/modules/swap/hooks/useSwapButtonContext.ts
index 4796cf66dd..632560b33f 100644
--- a/apps/cowswap-frontend/src/modules/swap/hooks/useSwapButtonContext.ts
+++ b/apps/cowswap-frontend/src/modules/swap/hooks/useSwapButtonContext.ts
@@ -132,7 +132,7 @@ export function useSwapButtonContext(input: SwapButtonInput): SwapButtonsContext
     isSwapUnsupported,
     isNativeIn: isNativeInSwap,
     wrappedToken,
-    quoteError: quote?.error,
+    quote,
     inputError: swapInputError,
     approvalState,
     feeWarningAccepted,
@@ -166,6 +166,6 @@ function useHasEnoughWrappedBalanceForSwap(inputAmount?: CurrencyAmount<Currency
   const { currencies } = useDerivedSwapInfo()
   const wrappedBalance = useCurrencyAmountBalance(currencies.INPUT ? getWrappedToken(currencies.INPUT) : undefined)
 
-  // is an native currency trade but wrapped token has enough balance
+  // is a native currency trade but wrapped token has enough balance
   return !!(wrappedBalance && inputAmount && !wrappedBalance.lessThan(inputAmount))
 }
diff --git a/apps/cowswap-frontend/src/modules/swap/pure/Row/RowFeeContent/index.cosmos.tsx b/apps/cowswap-frontend/src/modules/swap/pure/Row/RowFeeContent/index.cosmos.tsx
index 5bcf4fcbed..48655e490a 100644
--- a/apps/cowswap-frontend/src/modules/swap/pure/Row/RowFeeContent/index.cosmos.tsx
+++ b/apps/cowswap-frontend/src/modules/swap/pure/Row/RowFeeContent/index.cosmos.tsx
@@ -1,7 +1,7 @@
 import { COW, GNO } from '@cowprotocol/common-const'
 import { currencyAmountToTokenAmount } from '@cowprotocol/common-utils'
 import { SupportedChainId } from '@cowprotocol/cow-sdk'
-import { CurrencyAmount, TradeType, Price } from '@uniswap/sdk-core'
+import { CurrencyAmount, Price, TradeType } from '@uniswap/sdk-core'
 
 import TradeGp from 'legacy/state/swap/TradeGp'
 
@@ -20,7 +20,11 @@ const trade = new TradeGp({
   inputAmountWithoutFee: CurrencyAmount.fromRawAmount(currency, amount * 10 ** 18),
   outputAmount: CurrencyAmount.fromRawAmount(currency, output * 10 ** 18),
   outputAmountWithoutFee: CurrencyAmount.fromRawAmount(currency, (output - 3) * 10 ** 18),
-  fee: { feeAsCurrency: CurrencyAmount.fromRawAmount(currency, 3 * 10 ** 18), amount: '50' },
+  fee: {
+    feeAsCurrency: CurrencyAmount.fromRawAmount(currency, 3 * 10 ** 18),
+    amount: '50',
+    expirationDate: new Date().toISOString(),
+  },
   executionPrice: new Price(currency, currencyOut, 1, 4),
   tradeType: TradeType.EXACT_INPUT,
   quoteId: 10000,
diff --git a/apps/cowswap-frontend/src/modules/swap/pure/SwapButtons/index.tsx b/apps/cowswap-frontend/src/modules/swap/pure/SwapButtons/index.tsx
index b802be2ce1..b052629307 100644
--- a/apps/cowswap-frontend/src/modules/swap/pure/SwapButtons/index.tsx
+++ b/apps/cowswap-frontend/src/modules/swap/pure/SwapButtons/index.tsx
@@ -83,6 +83,11 @@ const swapButtonStateMap: { [key in SwapButtonState]: (props: SwapButtonsContext
       <Trans>Error loading price. Try again later.</Trans>
     </GreyCard>
   ),
+  [SwapButtonState.QuoteExpired]: () => (
+    <GreyCard style={{ textAlign: 'center' }}>
+      <Trans>Quote expired. Refreshing...</Trans>
+    </GreyCard>
+  ),
   [SwapButtonState.UnsupportedToken]: () => (
     <GreyCard style={{ textAlign: 'center' }}>
       <Trans>Unsupported token</Trans>
diff --git a/apps/cowswap-frontend/src/modules/swap/pure/TradeRates/index.cosmos.tsx b/apps/cowswap-frontend/src/modules/swap/pure/TradeRates/index.cosmos.tsx
index c23d86bc0f..c0c915b593 100644
--- a/apps/cowswap-frontend/src/modules/swap/pure/TradeRates/index.cosmos.tsx
+++ b/apps/cowswap-frontend/src/modules/swap/pure/TradeRates/index.cosmos.tsx
@@ -20,7 +20,11 @@ const trade = new TradeGp({
   inputAmountWithoutFee: CurrencyAmount.fromRawAmount(currency, amount * 10 ** 18),
   outputAmount: CurrencyAmount.fromRawAmount(currency, output * 10 ** 18),
   outputAmountWithoutFee: CurrencyAmount.fromRawAmount(currency, (output - 3) * 10 ** 18),
-  fee: { feeAsCurrency: CurrencyAmount.fromRawAmount(currency, 3 * 10 ** 18), amount: '50' },
+  fee: {
+    feeAsCurrency: CurrencyAmount.fromRawAmount(currency, 3 * 10 ** 18),
+    amount: '50',
+    expirationDate: new Date().toISOString(),
+  },
   executionPrice: new Price(currency, currencyOut, 1, 4),
   tradeType: TradeType.EXACT_INPUT,
   quoteId: 10000,
diff --git a/apps/cowswap-frontend/src/modules/swap/pure/TradeSummary/index.cosmos.tsx b/apps/cowswap-frontend/src/modules/swap/pure/TradeSummary/index.cosmos.tsx
index e6029d9b64..531636f97b 100644
--- a/apps/cowswap-frontend/src/modules/swap/pure/TradeSummary/index.cosmos.tsx
+++ b/apps/cowswap-frontend/src/modules/swap/pure/TradeSummary/index.cosmos.tsx
@@ -1,6 +1,6 @@
 import { COW, GNO } from '@cowprotocol/common-const'
 import { SupportedChainId } from '@cowprotocol/cow-sdk'
-import { CurrencyAmount, TradeType, Price, Percent } from '@uniswap/sdk-core'
+import { CurrencyAmount, Percent, Price, TradeType } from '@uniswap/sdk-core'
 
 import TradeGp from 'legacy/state/swap/TradeGp'
 
@@ -20,7 +20,11 @@ const trade = new TradeGp({
   inputAmountWithoutFee: CurrencyAmount.fromRawAmount(currency, amount * 10 ** 18),
   outputAmount: CurrencyAmount.fromRawAmount(currency, output * 10 ** 18),
   outputAmountWithoutFee: CurrencyAmount.fromRawAmount(currency, (output - 3) * 10 ** 18),
-  fee: { feeAsCurrency: CurrencyAmount.fromRawAmount(currency, 3 * 10 ** 18), amount: '50' },
+  fee: {
+    feeAsCurrency: CurrencyAmount.fromRawAmount(currency, 3 * 10 ** 18),
+    amount: '50',
+    expirationDate: new Date().toISOString(),
+  },
   executionPrice: new Price(currency, currencyOut, 1, 4),
   tradeType: TradeType.EXACT_INPUT,
   quoteId: 10000,
diff --git a/apps/cowswap-frontend/src/modules/swap/services/ethFlow/index.ts b/apps/cowswap-frontend/src/modules/swap/services/ethFlow/index.ts
index 8c2b32b226..994a58f4b6 100644
--- a/apps/cowswap-frontend/src/modules/swap/services/ethFlow/index.ts
+++ b/apps/cowswap-frontend/src/modules/swap/services/ethFlow/index.ts
@@ -1,4 +1,4 @@
-import { reportAppDataWithHooks } from '@cowprotocol/common-utils'
+import { reportAppDataWithHooks, reportPlaceOrderWithExpiredQuote } from '@cowprotocol/common-utils'
 import { CowEvents } from '@cowprotocol/events'
 import { Percent } from '@uniswap/sdk-core'
 
@@ -14,6 +14,7 @@ import { addPendingOrderStep } from 'modules/trade/utils/addPendingOrderStep'
 import { tradeFlowAnalytics } from 'modules/trade/utils/analytics'
 import { logTradeFlow } from 'modules/trade/utils/logger'
 import { getSwapErrorMessage } from 'modules/trade/utils/swapErrorHelper'
+import { isQuoteExpired } from 'modules/tradeQuote/utils/isQuoteExpired'
 
 import { calculateUniqueOrderId } from './steps/calculateUniqueOrderId'
 
@@ -36,7 +37,7 @@ export async function ethFlow(
     swapZeroFee,
   } = ethFlowContext
   const {
-    trade: { inputAmount, outputAmount },
+    trade: { inputAmount, outputAmount, fee },
   } = context
   const tradeAmounts = { inputAmount, outputAmount }
 
@@ -66,6 +67,12 @@ export async function ethFlow(
   )
 
   try {
+    // Do not proceed if fee is expired
+    if (isQuoteExpired(fee.expirationDate)) {
+      reportPlaceOrderWithExpiredQuote({ ...orderParamsOriginal, fee })
+      throw new Error('Quote expired. Please refresh.')
+    }
+
     logTradeFlow('ETH FLOW', 'STEP 4: sign order')
     const { order, txReceipt } = await signEthFlowOrderStep(orderId, orderParams, contract, addInFlightOrderId).finally(
       () => {
diff --git a/apps/cowswap-frontend/src/modules/tradeFormValidation/pure/TradeFormButtons/tradeButtonsMap.tsx b/apps/cowswap-frontend/src/modules/tradeFormValidation/pure/TradeFormButtons/tradeButtonsMap.tsx
index 19dbfa1523..84f624b44e 100644
--- a/apps/cowswap-frontend/src/modules/tradeFormValidation/pure/TradeFormButtons/tradeButtonsMap.tsx
+++ b/apps/cowswap-frontend/src/modules/tradeFormValidation/pure/TradeFormButtons/tradeButtonsMap.tsx
@@ -96,6 +96,7 @@ export const tradeButtonsMap: Record<TradeFormValidation, ButtonErrorConfig | Bu
       </TradeFormBlankButton>
     )
   },
+  [TradeFormValidation.QuoteExpired]: { text: 'Quote expired. Refreshing...' },
   [TradeFormValidation.WalletNotConnected]: (context) => {
     return (
       <TradeFormBlankButton onClick={context.connectWallet || undefined} disabled={!context.connectWallet}>
diff --git a/apps/cowswap-frontend/src/modules/tradeFormValidation/services/validateTradeForm.ts b/apps/cowswap-frontend/src/modules/tradeFormValidation/services/validateTradeForm.ts
index 9fe854ae6f..2767e3e935 100644
--- a/apps/cowswap-frontend/src/modules/tradeFormValidation/services/validateTradeForm.ts
+++ b/apps/cowswap-frontend/src/modules/tradeFormValidation/services/validateTradeForm.ts
@@ -1,5 +1,8 @@
 import { getIsNativeToken, isAddress, isFractionFalsy } from '@cowprotocol/common-utils'
 
+import { TradeType } from 'modules/trade'
+import { isQuoteExpired } from 'modules/tradeQuote/utils/isQuoteExpired'
+
 import { ApprovalState } from 'common/hooks/useApproveState'
 
 import { TradeFormValidation, TradeFormValidationContext } from '../types'
@@ -88,5 +91,14 @@ export function validateTradeForm(context: TradeFormValidationContext): TradeFor
     return TradeFormValidation.ApproveRequired
   }
 
+  if (
+    !isWrapUnwrap &&
+    derivedTradeState.tradeType !== TradeType.LIMIT_ORDER &&
+    !tradeQuote.isLoading &&
+    isQuoteExpired(tradeQuote.response?.expiration) === true
+  ) {
+    return TradeFormValidation.QuoteExpired
+  }
+
   return null
 }
diff --git a/apps/cowswap-frontend/src/modules/tradeFormValidation/types.ts b/apps/cowswap-frontend/src/modules/tradeFormValidation/types.ts
index d2cbfad2b9..ea3cc9364c 100644
--- a/apps/cowswap-frontend/src/modules/tradeFormValidation/types.ts
+++ b/apps/cowswap-frontend/src/modules/tradeFormValidation/types.ts
@@ -25,6 +25,7 @@ export enum TradeFormValidation {
 
   // Quote loading indicator
   QuoteLoading,
+  QuoteExpired,
 
   // Balances
   BalancesNotLoaded,
diff --git a/apps/cowswap-frontend/src/modules/tradeQuote/utils/isQuoteExpired.ts b/apps/cowswap-frontend/src/modules/tradeQuote/utils/isQuoteExpired.ts
new file mode 100644
index 0000000000..8b7c8bc4ff
--- /dev/null
+++ b/apps/cowswap-frontend/src/modules/tradeQuote/utils/isQuoteExpired.ts
@@ -0,0 +1,14 @@
+import ms from 'ms.macro'
+import { Nullish } from 'types'
+
+const EXPIRATION_TIME_DELTA = ms`5s`
+
+export function isQuoteExpired(expirationDate: Nullish<string>): boolean | undefined {
+  if (!expirationDate) {
+    return undefined
+  }
+
+  const expirationTime = new Date(expirationDate).getTime()
+
+  return Date.now() > expirationTime - EXPIRATION_TIME_DELTA
+}
diff --git a/libs/common-utils/src/sentry.ts b/libs/common-utils/src/sentry.ts
index 90745bce86..06636f5d01 100644
--- a/libs/common-utils/src/sentry.ts
+++ b/libs/common-utils/src/sentry.ts
@@ -15,3 +15,10 @@ export function reportAppDataWithHooks(params: Record<any, any>): void {
     contexts: { params },
   })
 }
+
+export function reportPlaceOrderWithExpiredQuote(params: Record<any, any>): void {
+  Sentry.captureException('Attempt to place order with expired quote', {
+    tags: { errorType: 'placeOrderWithExpiredQuote' },
+    contexts: { params },
+  })
+}