diff --git a/packages/vite/src/node/plugins/importAnalysis.ts b/packages/vite/src/node/plugins/importAnalysis.ts
index 2b7fcc6185db54..995bffbcf49985 100644
--- a/packages/vite/src/node/plugins/importAnalysis.ts
+++ b/packages/vite/src/node/plugins/importAnalysis.ts
@@ -307,6 +307,11 @@ export function importAnalysisPlugin(config: ResolvedConfig): Plugin {
         return [url, resolved.id]
       }
 
+      // Import rewrites, we do them after all the URLs have been resolved
+      // to help with the discovery of new dependencies. If we need to wait
+      // for each dependency there could be one reload per import
+      const importRewrites: (() => Promise<void>)[] = []
+
       for (let index = 0; index < imports.length; index++) {
         const {
           s: start,
@@ -433,61 +438,67 @@ export function importAnalysisPlugin(config: ResolvedConfig): Plugin {
           // record as safe modules
           server?.moduleGraph.safeModulesPath.add(fsPathFromUrl(url))
 
-          // rewrite
           if (url !== specifier) {
-            let rewriteDone = false
-            if (
-              isOptimizedDepFile(resolvedId, config) &&
-              !resolvedId.match(optimizedDepChunkRE)
-            ) {
-              // for optimized cjs deps, support named imports by rewriting named imports to const assignments.
-              // internal optimized chunks don't need es interop and are excluded
-
-              // The browserHash in resolvedId could be stale in which case there will be a full
-              // page reload. We could return a 404 in that case but it is safe to return the request
-              const file = cleanUrl(resolvedId) // Remove ?v={hash}
-
-              const needsInterop = await optimizedDepNeedsInterop(
-                server._optimizeDepsMetadata!,
-                file
-              )
-
-              if (needsInterop === undefined) {
-                // Non-entry dynamic imports from dependencies will reach here as there isn't
-                // optimize info for them, but they don't need es interop. If the request isn't
-                // a dynamic import, then it is an internal Vite error
-                if (!file.match(optimizedDepDynamicRE)) {
-                  config.logger.error(
-                    colors.red(
-                      `Vite Error, ${url} optimized info should be defined`
+            importRewrites.push(async () => {
+              let rewriteDone = false
+              if (
+                isOptimizedDepFile(resolvedId, config) &&
+                !resolvedId.match(optimizedDepChunkRE)
+              ) {
+                // for optimized cjs deps, support named imports by rewriting named imports to const assignments.
+                // internal optimized chunks don't need es interop and are excluded
+
+                // The browserHash in resolvedId could be stale in which case there will be a full
+                // page reload. We could return a 404 in that case but it is safe to return the request
+                const file = cleanUrl(resolvedId) // Remove ?v={hash}
+
+                const needsInterop = await optimizedDepNeedsInterop(
+                  server._optimizeDepsMetadata!,
+                  file
+                )
+
+                if (needsInterop === undefined) {
+                  // Non-entry dynamic imports from dependencies will reach here as there isn't
+                  // optimize info for them, but they don't need es interop. If the request isn't
+                  // a dynamic import, then it is an internal Vite error
+                  if (!file.match(optimizedDepDynamicRE)) {
+                    config.logger.error(
+                      colors.red(
+                        `Vite Error, ${url} optimized info should be defined`
+                      )
+                    )
+                  }
+                } else if (needsInterop) {
+                  debug(`${url} needs interop`)
+                  if (isDynamicImport) {
+                    // rewrite `import('package')` to expose the default directly
+                    str().overwrite(
+                      dynamicIndex,
+                      end + 1,
+                      `import('${url}').then(m => m.default && m.default.__esModule ? m.default : ({ ...m.default, default: m.default }))`
                     )
-                  )
-                }
-              } else if (needsInterop) {
-                debug(`${url} needs interop`)
-                if (isDynamicImport) {
-                  // rewrite `import('package')` to expose the default directly
-                  str().overwrite(
-                    dynamicIndex,
-                    end + 1,
-                    `import('${url}').then(m => m.default && m.default.__esModule ? m.default : ({ ...m.default, default: m.default }))`
-                  )
-                } else {
-                  const exp = source.slice(expStart, expEnd)
-                  const rewritten = transformCjsImport(exp, url, rawUrl, index)
-                  if (rewritten) {
-                    str().overwrite(expStart, expEnd, rewritten)
                   } else {
-                    // #1439 export * from '...'
-                    str().overwrite(start, end, url)
+                    const exp = source.slice(expStart, expEnd)
+                    const rewritten = transformCjsImport(
+                      exp,
+                      url,
+                      rawUrl,
+                      index
+                    )
+                    if (rewritten) {
+                      str().overwrite(expStart, expEnd, rewritten)
+                    } else {
+                      // #1439 export * from '...'
+                      str().overwrite(start, end, url)
+                    }
                   }
+                  rewriteDone = true
                 }
-                rewriteDone = true
               }
-            }
-            if (!rewriteDone) {
-              str().overwrite(start, end, isDynamicImport ? `'${url}'` : url)
-            }
+              if (!rewriteDone) {
+                str().overwrite(start, end, isDynamicImport ? `'${url}'` : url)
+              }
+            })
           }
 
           // record for HMR import chain analysis
@@ -642,6 +653,14 @@ export function importAnalysisPlugin(config: ResolvedConfig): Plugin {
         })
       }
 
+      // Await for import rewrites that requires dependencies to be pre-bundled to
+      // know if es interop is needed after starting further transformRequest calls
+      // This will let Vite process deeper into the user code and find more missing
+      // dependencies before the next page reload
+      for (const rewrite of importRewrites) {
+        await rewrite()
+      }
+
       if (s) {
         return s.toString()
       } else {