diff --git a/okhttp-testing-support/src/main/kotlin/okhttp3/internal/http/RecordingProxySelector.kt b/okhttp-testing-support/src/main/kotlin/okhttp3/internal/http/RecordingProxySelector.kt
index b81d99857..a51e8afb7 100644
--- a/okhttp-testing-support/src/main/kotlin/okhttp3/internal/http/RecordingProxySelector.kt
+++ b/okhttp-testing-support/src/main/kotlin/okhttp3/internal/http/RecordingProxySelector.kt
@@ -30,8 +30,8 @@ import okhttp3.internal.format
 class RecordingProxySelector : ProxySelector() {
   @JvmField val proxies = mutableListOf<Proxy>()
 
-  private val requestedUris = mutableListOf<URI>()
-  private val failures = mutableListOf<String>()
+  val requestedUris = mutableListOf<URI>()
+  val failures = mutableListOf<String>()
 
   override fun select(uri: URI): List<Proxy> {
     requestedUris.add(uri)
diff --git a/okhttp/src/main/kotlin/okhttp3/internal/connection/ConnectPlan.kt b/okhttp/src/main/kotlin/okhttp3/internal/connection/ConnectPlan.kt
index b143092cc..a2815f5c1 100644
--- a/okhttp/src/main/kotlin/okhttp3/internal/connection/ConnectPlan.kt
+++ b/okhttp/src/main/kotlin/okhttp3/internal/connection/ConnectPlan.kt
@@ -141,6 +141,14 @@ class ConnectPlan(
       success = true
       return ConnectResult(plan = this)
     } catch (e: IOException) {
+      // If we used the ProxySelector, and got a IOException during connect, report the failure.
+      if (route.address.proxy == null && route.proxy.type() != Proxy.Type.DIRECT) {
+        route.address.proxySelector.connectFailed(
+          route.address.url.toUri(),
+          route.proxy.address(),
+          e,
+        )
+      }
       user.connectFailed(route, null, e)
       return ConnectResult(plan = this, throwable = e)
     } finally {
diff --git a/okhttp/src/test/java/okhttp3/CallTest.kt b/okhttp/src/test/java/okhttp3/CallTest.kt
index 47d1dc91d..c483e5843 100644
--- a/okhttp/src/test/java/okhttp3/CallTest.kt
+++ b/okhttp/src/test/java/okhttp3/CallTest.kt
@@ -15,11 +15,14 @@
  */
 package okhttp3
 
+import assertk.all
 import assertk.assertThat
 import assertk.assertions.contains
 import assertk.assertions.containsExactly
 import assertk.assertions.doesNotContain
 import assertk.assertions.hasMessage
+import assertk.assertions.hasSize
+import assertk.assertions.index
 import assertk.assertions.isCloseTo
 import assertk.assertions.isEmpty
 import assertk.assertions.isEqualTo
@@ -30,6 +33,7 @@ import assertk.assertions.isNotNull
 import assertk.assertions.isNotSameAs
 import assertk.assertions.isNull
 import assertk.assertions.isTrue
+import assertk.assertions.matches
 import assertk.assertions.startsWith
 import assertk.fail
 import java.io.FileNotFoundException
@@ -1017,6 +1021,12 @@ open class CallTest {
     executeSynchronously(request)
       .assertCode(200)
       .assertBody("success!")
+
+    assertThat(proxySelector.failures)
+      .all {
+        hasSize(1)
+        index(0).matches(".* Connect timed out".toRegex(RegexOption.IGNORE_CASE))
+      }
   }
 
   /** https://github.com/square/okhttp/issues/4875  */