diff --git a/xplat/Flipper/ConnectionContextStore.cpp b/xplat/Flipper/ConnectionContextStore.cpp
index 514eef14f..ffcf2d515 100644
--- a/xplat/Flipper/ConnectionContextStore.cpp
+++ b/xplat/Flipper/ConnectionContextStore.cpp
@@ -6,6 +6,7 @@
  */
 
 #include "ConnectionContextStore.h"
+#include <folly/Optional.h>
 #include <folly/json.h>
 #include <folly/portability/SysStat.h>
 #include <openssl/err.h>
@@ -110,6 +111,21 @@ std::string ConnectionContextStore::getDeviceId() {
   }
 }
 
+folly::Optional<FlipperCertificateExchangeMedium>
+ConnectionContextStore::getLastKnownMedium() {
+  try {
+    std::string config =
+        loadStringFromFile(absoluteFilePath(CONNECTION_CONFIG_FILE));
+    auto maybeMedium = folly::parseJson(config)["medium"];
+    return maybeMedium.isInt()
+        ? folly::Optional<FlipperCertificateExchangeMedium>{static_cast<
+              FlipperCertificateExchangeMedium>(maybeMedium.getInt())}
+        : folly::none;
+  } catch (std::exception&) {
+    return folly::none;
+  }
+}
+
 void ConnectionContextStore::storeConnectionConfig(folly::dynamic& config) {
   std::string json = folly::toJson(config);
   writeStringToFile(json, absoluteFilePath(CONNECTION_CONFIG_FILE));
diff --git a/xplat/Flipper/ConnectionContextStore.h b/xplat/Flipper/ConnectionContextStore.h
index a8a2b0eb1..bc13898b4 100644
--- a/xplat/Flipper/ConnectionContextStore.h
+++ b/xplat/Flipper/ConnectionContextStore.h
@@ -7,9 +7,11 @@
 
 #pragma once
 
+#include <folly/Optional.h>
 #include <folly/dynamic.h>
 #include <folly/io/async/SSLContext.h>
 #include <string>
+#include "FlipperCertificateExchangeMedium.h"
 #include "FlipperInitConfig.h"
 
 namespace facebook {
@@ -24,6 +26,10 @@ class ConnectionContextStore {
   std::string getCertificateDirectoryPath();
   std::string getCACertificatePath();
   std::string getDeviceId();
+  /**
+   * Get medium over which the certificate was received.
+   */
+  folly::Optional<FlipperCertificateExchangeMedium> getLastKnownMedium();
   void storeConnectionConfig(folly::dynamic& config);
   bool resetState();
 
diff --git a/xplat/Flipper/FlipperCertificateExchangeMedium.h b/xplat/Flipper/FlipperCertificateExchangeMedium.h
index 552b081e5..0604dcd68 100644
--- a/xplat/Flipper/FlipperCertificateExchangeMedium.h
+++ b/xplat/Flipper/FlipperCertificateExchangeMedium.h
@@ -5,4 +5,6 @@
  * LICENSE file in the root directory of this source tree.
  */
 
+#pragma once
+
 enum FlipperCertificateExchangeMedium { FS_ACCESS = 1, WWW = 2 };
diff --git a/xplat/Flipper/FlipperConnectionManagerImpl.cpp b/xplat/Flipper/FlipperConnectionManagerImpl.cpp
index 506db8580..a5ab36a35 100644
--- a/xplat/Flipper/FlipperConnectionManagerImpl.cpp
+++ b/xplat/Flipper/FlipperConnectionManagerImpl.cpp
@@ -357,6 +357,21 @@ bool FlipperConnectionManagerImpl::isCertificateExchangeNeeded() {
     return true;
   }
 
+  auto last_known_medium = contextStore_->getLastKnownMedium();
+  if (!last_known_medium) {
+    return true;
+  }
+
+  // When we exchange certs over WWW, we use a fake generated serial number and
+  // a virtual device. If medium changes to FS_ACCESS at some point, we should
+  // restart the exchange process to get the device ID of the real device.
+  int medium = certProvider_ != nullptr
+      ? certProvider_->getCertificateExchangeMedium()
+      : FlipperCertificateExchangeMedium::FS_ACCESS;
+  if (last_known_medium != medium) {
+    return true;
+  }
+
   auto step = flipperState_->start("Check required certificates are present");
   bool hasRequiredFiles = contextStore_->hasRequiredFiles();
   if (hasRequiredFiles) {
@@ -380,10 +395,10 @@ void FlipperConnectionManagerImpl::requestSignedCertFromFlipper() {
 
   certificateExchangeCompleted_ = false;
 
-  flipperEventBase_->add([this, message, gettingCert]() {
+  flipperEventBase_->add([this, message, gettingCert, medium]() {
     client_->sendExpectResponse(
         folly::toJson(message),
-        [this, message, gettingCert](
+        [this, message, gettingCert, medium](
             const std::string& response, bool isError) {
           /**
             Need to keep track of whether the response has been handled.
@@ -412,6 +427,7 @@ void FlipperConnectionManagerImpl::requestSignedCertFromFlipper() {
           }
           if (!response.empty()) {
             folly::dynamic config = folly::parseJson(response);
+            config["medium"] = medium;
             contextStore_->storeConnectionConfig(config);
           }
           if (certProvider_) {