diff --git a/src/utils/shell.ts b/src/utils/shell.ts
index 62f8adbf95e..b526bbf9d6f 100644
--- a/src/utils/shell.ts
+++ b/src/utils/shell.ts
@@ -12,6 +12,47 @@ import { processOnExit } from './dev.js'
 const isErrnoException = (value: unknown): value is NodeJS.ErrnoException =>
   value instanceof Error && Object.hasOwn(value, 'code')
 
+type CommandResult = {
+  exitCode?: number
+  message?: string
+  shortMessage?: string
+  stderr?: string
+  stdout?: string
+}
+
+const isCommandResult = (value: unknown): value is CommandResult =>
+  typeof value === 'object' &&
+  value !== null &&
+  (typeof (value as CommandResult).exitCode === 'number' ||
+    typeof (value as CommandResult).message === 'string' ||
+    typeof (value as CommandResult).shortMessage === 'string' ||
+    typeof (value as CommandResult).stderr === 'string' ||
+    typeof (value as CommandResult).stdout === 'string')
+
+export const getCommandName = (command: string) => {
+  const match = /^(?:"([^"]+)"|'([^']+)'|(\S+))/.exec(command.trim())
+
+  return match?.[1] ?? match?.[2] ?? match?.[3] ?? command
+}
+
+export const canReportMissingCommandName = (command: string) =>
+  !/(?:&&|\|\||[|;<>])/.test(command) && !/^\s*[\w.-]+=/.test(command)
+
+export const shouldUseShell = (command: string) =>
+  /(?:&&|\|\||[|;<>])/.test(command) || /^\s*[\w.-]+=(?:"[^"]*"|'[^']*'|\S+)\s+\S/.test(command)
+
+const isMissingCommandMessage = ({ command, output }: { command: string; output: string }) =>
+  output.split(/\r?\n/).some((line) => {
+    const normalizedLine = line.toLowerCase()
+    const normalizedCommand = command.toLowerCase()
+
+    return (
+      normalizedLine.includes(normalizedCommand) &&
+      (normalizedLine.includes('not found') ||
+        normalizedLine.includes('is not recognized as an internal or external command'))
+    )
+  })
+
 const createStripAnsiControlCharsStream = (): Transform =>
   new Transform({
     transform(chunk, _encoding, callback) {
@@ -68,6 +109,7 @@ export const runCommand = (
   const { cwd, env = {}, spinner } = options
   const commandProcess = execa.command(command, {
     preferLocal: true,
+    shell: shouldUseShell(command),
     // we use reject=false to avoid rejecting synchronously when the command doesn't exist
     reject: false,
     env: {
@@ -111,8 +153,12 @@ export const runCommand = (
   // eslint-disable-next-line @typescript-eslint/no-floating-promises
   commandProcess.then(async () => {
     const result = await commandProcess
-    const [commandWithoutArgs] = command.split(' ')
-    if (result.failed && isNonExistingCommandError({ command: commandWithoutArgs, error: result })) {
+    const commandWithoutArgs = getCommandName(command)
+    if (
+      result.failed &&
+      canReportMissingCommandName(command) &&
+      isNonExistingCommandError({ command: commandWithoutArgs, error: result })
+    ) {
       log(
         `${NETLIFYDEVERR} Failed running command: ${command}. Please verify ${chalk.magenta(
           `'${commandWithoutArgs}'`,
@@ -135,7 +181,7 @@ export const runCommand = (
   return commandProcess
 }
 
-const isNonExistingCommandError = ({ command, error: commandError }: { command: string; error: unknown }) => {
+export const isNonExistingCommandError = ({ command, error: commandError }: { command: string; error: unknown }) => {
   // `ENOENT` is only returned for non Windows systems
   // See https://github.com/sindresorhus/execa/pull/447
   if (isErrnoException(commandError) && commandError.code === 'ENOENT') {
@@ -147,10 +193,13 @@ const isNonExistingCommandError = ({ command, error: commandError }: { command:
     return false
   }
 
-  // this only works on English versions of Windows
-  return (
-    commandError instanceof Error &&
-    typeof commandError.message === 'string' &&
-    commandError.message.includes('is not recognized as an internal or external command')
-  )
+  if (!isCommandResult(commandError)) {
+    return false
+  }
+
+  const output = [commandError.message, commandError.shortMessage, commandError.stderr, commandError.stdout]
+    .filter((value): value is string => typeof value === 'string')
+    .join('\n')
+
+  return isMissingCommandMessage({ command, output })
 }
diff --git a/tests/integration/framework-detection.test.ts b/tests/integration/framework-detection.test.ts
index fe32530e507..4d55eba5ff5 100644
--- a/tests/integration/framework-detection.test.ts
+++ b/tests/integration/framework-detection.test.ts
@@ -130,6 +130,25 @@ describe.concurrent('frameworks/framework-detection', () => {
     })
   })
 
+  test('should support shell operators in `command`', async (t) => {
+    await withSiteBuilder(t, async (builder) => {
+      await builder
+        .withNetlifyToml({ config: { dev: { command: 'echo first && echo second', targetPort: 3000 } } })
+        .build()
+
+      try {
+        await withDevServer({ cwd: builder.directory }, async () => {}, true)
+        // a failure is expected since this command does not start a server
+        t.expect.unreachable()
+      } catch (err) {
+        t.expect(err).toHaveProperty('stdout')
+        const output = normalizeSnapshot((err as execa.ExecaReturnValue).stdout, { duration: true, filePath: true })
+        t.expect(output).toMatch(/\nfirst[^\S\r\n]*\r?\n[^\S\r\n]*second\r?\n/i)
+        t.expect(output).not.toMatch(/\nfirst[^\S\r\n]*&&[^\S\r\n]*echo[^\S\r\n]+second\r?\n/i)
+      }
+    })
+  })
+
   test('should force a specific framework when configured', async (t) => {
     await withSiteBuilder(t, async (builder) => {
       await builder.withNetlifyToml({ config: { dev: { framework: 'create-react-app' } } }).build()
diff --git a/tests/unit/utils/shell.test.ts b/tests/unit/utils/shell.test.ts
new file mode 100644
index 00000000000..ba44276b20c
--- /dev/null
+++ b/tests/unit/utils/shell.test.ts
@@ -0,0 +1,54 @@
+import { describe, expect, test } from 'vitest'
+
+import {
+  canReportMissingCommandName,
+  getCommandName,
+  isNonExistingCommandError,
+  shouldUseShell,
+} from '../../../src/utils/shell.js'
+
+describe('shell command helpers', () => {
+  test('uses a shell only when command syntax requires it', () => {
+    expect(shouldUseShell('npm run dev')).toBe(false)
+    expect(shouldUseShell('echo first && echo second')).toBe(true)
+    expect(shouldUseShell('npm run build || npm run fallback')).toBe(true)
+    expect(shouldUseShell('FOO=1 npm run dev')).toBe(true)
+  })
+
+  test('extracts quoted and unquoted command names', () => {
+    expect(getCommandName('npm run dev')).toBe('npm')
+    expect(getCommandName('"my command" --flag')).toBe('my command')
+    expect(getCommandName("'my command' --flag")).toBe('my command')
+  })
+
+  test('does not report a single missing command for compound shell syntax', () => {
+    expect(canReportMissingCommandName('npm run dev')).toBe(true)
+    expect(canReportMissingCommandName('echo before && missing-command')).toBe(false)
+    expect(canReportMissingCommandName('FOO=1 missing-command')).toBe(false)
+  })
+
+  test('detects missing command output without treating package managers as missing commands', () => {
+    expect(
+      isNonExistingCommandError({
+        command: 'missing-command',
+        error: { stderr: 'sh: missing-command: command not found', exitCode: 127 },
+      }),
+    ).toBe(true)
+
+    expect(
+      isNonExistingCommandError({
+        command: 'npm',
+        error: { stderr: 'sh: npm: command not found', exitCode: 127 },
+      }),
+    ).toBe(false)
+  })
+
+  test('does not classify an existing command exit 127 as a missing command', () => {
+    expect(
+      isNonExistingCommandError({
+        command: 'bash',
+        error: { shortMessage: 'Command failed with exit code 127: bash -c "exit 127"', exitCode: 127 },
+      }),
+    ).toBe(false)
+  })
+})