diff --git a/CHANGELOG.md b/CHANGELOG.md
index da49e486cb1..ef9cc8e2795 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -13,6 +13,17 @@
 - Quartz `SentryJobListener` can send a monitor config derived from the trigger with check-ins, so Sentry creates or updates the monitor from code. Set the `sentry-upsert-monitor-config` job or trigger data key to `"true"` to send the schedule ([#6216](https://github.com/getsentry/sentry-java/pull/6216))
 - Send a monitor config derived from Spring `@Scheduled` with `@SentryCheckIn` check-ins, so Sentry creates or updates the monitor from code. Set `@SentryCheckIn(upsertMonitorConfig = true)` to send the schedule ([#6215](https://github.com/getsentry/sentry-java/pull/6215))
 
+### Fixes
+
+- Stop marking an OkHttp call span as failed when a connection attempt to one of the host's addresses fails but OkHttp connects on another ([#6472](https://github.com/getsentry/sentry-java/pull/6472))
+
+### Dependencies
+
+- Bump OkHttp from 4.9.2 to 5.5.1 ([#6472](https://github.com/getsentry/sentry-java/pull/6472))
+  - `sentry-okhttp` and the Spring Boot integrations keep OkHttp as a `compileOnly` dependency, so your app keeps the OkHttp version it declares. OkHttp 4 is still supported.
+  - [changelog](https://github.com/square/okhttp/blob/master/CHANGELOG.md)
+  - [diff](https://github.com/square/okhttp/compare/parent-4.9.2...parent-5.5.1)
+
 ## 8.63.0
 
 ### Features
diff --git a/gradle/libs.versions.toml b/gradle/libs.versions.toml
index c4a98a0f115..25681bf9137 100644
--- a/gradle/libs.versions.toml
+++ b/gradle/libs.versions.toml
@@ -27,7 +27,7 @@ log4j2 = "2.26.1"
 nopen = "1.0.1"
 # see https://www.jetbrains.com/help/kotlin-multiplatform-dev/compose-compatibility-and-versioning.html#kotlin-compatibility
 # see https://developer.android.com/jetpack/androidx/releases/compose-kotlin
-okhttp = "4.9.2"
+okhttp = "5.5.1"
 openfeature = "1.18.2"
 otel = "1.63.0"
 otelAlpha = "1.63.0-alpha"
@@ -295,9 +295,11 @@ mockito-kotlin = { module = "org.mockito.kotlin:mockito-kotlin", version = "6.4.
 mockito-core = { module = "org.mockito:mockito-core", version = "5.24.0" }
 msgpack = { module = "org.msgpack:msgpack-core", version = "0.9.8" }
 okhttp-mockwebserver = { module = "com.squareup.okhttp3:mockwebserver", version.ref = "okhttp" }
+# For tests that can't run on okhttp 5: apollo-runtime 2.x passes a null body to
+# Response.Builder.body(), and the Android UI tests are pinned to leakcanary's okio 2, while okhttp
+# 5 needs okio 3.
+okhttp-mockwebserver4 = { module = "com.squareup.okhttp3:mockwebserver", version = "4.9.2" }
 okhttp-tls = { module = "com.squareup.okhttp3:okhttp-tls", version.ref = "okhttp" }
-# apollo-runtime 5.x pulls in okhttp 5.x; mockwebserver 4.x is incompatible with that classpath
-okhttp-mockwebserver5 = { module = "com.squareup.okhttp3:mockwebserver", version = "5.3.0" }
 okio = { module = "com.squareup.okio:okio", version = "1.13.0" }
 roboelectric = { module = "org.robolectric:robolectric", version = "4.15" }
 
diff --git a/sentry-android-integration-tests/sentry-uitest-android/build.gradle.kts b/sentry-android-integration-tests/sentry-uitest-android/build.gradle.kts
index d67f29648a4..7bbbe39e04f 100644
--- a/sentry-android-integration-tests/sentry-uitest-android/build.gradle.kts
+++ b/sentry-android-integration-tests/sentry-uitest-android/build.gradle.kts
@@ -124,7 +124,7 @@ dependencies {
   androidTestImplementation(libs.awaitility3.kotlin)
   androidTestImplementation(libs.kotlin.test.junit)
   androidTestImplementation(libs.leakcanary.instrumentation)
-  androidTestImplementation(libs.okhttp.mockwebserver)
+  androidTestImplementation(libs.okhttp.mockwebserver4)
 }
 
 tasks.withType<JavaCompile>().configureEach {
diff --git a/sentry-apollo-5/build.gradle.kts b/sentry-apollo-5/build.gradle.kts
index 3078d833294..47db9da4984 100644
--- a/sentry-apollo-5/build.gradle.kts
+++ b/sentry-apollo-5/build.gradle.kts
@@ -42,7 +42,7 @@ dependencies {
   testImplementation(libs.kotlinx.coroutines.test)
   testImplementation(libs.mockito.kotlin)
   testImplementation(libs.mockito.core)
-  testImplementation(libs.okhttp.mockwebserver5)
+  testImplementation(libs.okhttp.mockwebserver)
 }
 
 tasks.withType<JavaCompile>().configureEach {
diff --git a/sentry-apollo/build.gradle.kts b/sentry-apollo/build.gradle.kts
index 809b7f3a75c..e11b91a4c29 100644
--- a/sentry-apollo/build.gradle.kts
+++ b/sentry-apollo/build.gradle.kts
@@ -43,7 +43,7 @@ dependencies {
   testImplementation(libs.kotlinx.coroutines)
   testImplementation(libs.mockito.kotlin)
   testImplementation(libs.mockito.core)
-  testImplementation(libs.okhttp.mockwebserver)
+  testImplementation(libs.okhttp.mockwebserver4)
 }
 
 tasks.withType<JavaCompile>().configureEach {
diff --git a/sentry-okhttp/src/main/java/io/sentry/okhttp/SentryOkHttpEventListener.kt b/sentry-okhttp/src/main/java/io/sentry/okhttp/SentryOkHttpEventListener.kt
index b43fcfdfb66..12836a732b0 100644
--- a/sentry-okhttp/src/main/java/io/sentry/okhttp/SentryOkHttpEventListener.kt
+++ b/sentry-okhttp/src/main/java/io/sentry/okhttp/SentryOkHttpEventListener.kt
@@ -245,11 +245,9 @@ public open class SentryOkHttpEventListener(
     }
     val okHttpEvent: SentryOkHttpEvent = eventMap[call] ?: return
     okHttpEvent.setProtocol(protocol?.name)
-    okHttpEvent.setError(ioe.message)
-    okHttpEvent.onEventFinish(CONNECT_EVENT) {
-      it.throwable = ioe
-      it.status = SpanStatus.INTERNAL_ERROR
-    }
+    // A failed route doesn't fail the call: OkHttp moves on to the next route, and OkHttp 5 races
+    // routes for Happy Eyeballs. If no route connects, callFailed() reports the error.
+    okHttpEvent.onEventFinish(CONNECT_EVENT)
   }
 
   override fun connectionAcquired(call: Call, connection: Connection) {
diff --git a/sentry-okhttp/src/test/java/io/sentry/okhttp/SentryOkHttpEventListenerTest.kt b/sentry-okhttp/src/test/java/io/sentry/okhttp/SentryOkHttpEventListenerTest.kt
index e4772145879..7f9915f13b1 100644
--- a/sentry-okhttp/src/test/java/io/sentry/okhttp/SentryOkHttpEventListenerTest.kt
+++ b/sentry-okhttp/src/test/java/io/sentry/okhttp/SentryOkHttpEventListenerTest.kt
@@ -1,5 +1,6 @@
 package io.sentry.okhttp
 
+import com.google.common.truth.Truth.assertThat
 import io.sentry.BaggageHeader
 import io.sentry.IScopes
 import io.sentry.SentryOptions
@@ -9,6 +10,7 @@ import io.sentry.SpanDataConvention
 import io.sentry.SpanStatus
 import io.sentry.TransactionContext
 import io.sentry.mockServerRequestTimeoutMillis
+import java.io.IOException
 import java.util.concurrent.TimeUnit
 import kotlin.test.Test
 import kotlin.test.assertEquals
@@ -26,7 +28,6 @@ import okhttp3.mockwebserver.MockResponse
 import okhttp3.mockwebserver.MockWebServer
 import okhttp3.mockwebserver.SocketPolicy
 import org.mockito.kotlin.any
-import org.mockito.kotlin.anyOrNull
 import org.mockito.kotlin.eq
 import org.mockito.kotlin.mock
 import org.mockito.kotlin.spy
@@ -281,7 +282,7 @@ class SentryOkHttpEventListenerTest {
   fun `call span status is not overridden if not null`() {
     val mockListener = mock<EventListener>()
     lateinit var call: Call
-    whenever(mockListener.connectStart(any(), anyOrNull(), anyOrNull())).then {
+    whenever(mockListener.requestHeadersStart(any())).then {
       val okHttpEvent = SentryOkHttpEventListener.eventMap[call]
       val callSpan = okHttpEvent?.callSpan
       assertNotNull(callSpan)
@@ -300,6 +301,48 @@ class SentryOkHttpEventListenerTest {
     assertEquals(SpanStatus.UNKNOWN, callSpan.status)
   }
 
+  @Test
+  fun `a failed route does not fail the call when the next route connects`() {
+    val sut = fixture.getSut()
+    val listener = fixture.sentryOkHttpEventListener
+    val call = sut.newCall(getRequest())
+    val response = mock<Response>()
+    whenever(response.code).thenReturn(200)
+    whenever(response.protocol).thenReturn(Protocol.HTTP_1_1)
+
+    listener.callStart(call)
+    listener.connectStart(call, mock(), mock())
+    listener.connectFailed(call, mock(), mock(), null, IOException("Connection refused"))
+    listener.connectStart(call, mock(), mock())
+    listener.connectEnd(call, mock(), mock(), Protocol.HTTP_1_1)
+    listener.responseHeadersStart(call)
+    listener.responseHeadersEnd(call, response)
+    val callSpan = SentryOkHttpEventListener.eventMap[call]!!.callSpan!!
+    listener.callEnd(call)
+
+    assertThat(callSpan.status).isEqualTo(SpanStatus.OK)
+    assertThat(callSpan.throwable).isNull()
+    assertThat(callSpan.getData("error_message")).isNull()
+  }
+
+  @Test
+  fun `a call that fails to connect on every route is marked as failed`() {
+    val sut = fixture.getSut()
+    val listener = fixture.sentryOkHttpEventListener
+    val call = sut.newCall(getRequest())
+    val error = IOException("Connection refused")
+
+    listener.callStart(call)
+    listener.connectStart(call, mock(), mock())
+    listener.connectFailed(call, mock(), mock(), null, error)
+    val callSpan = SentryOkHttpEventListener.eventMap[call]!!.callSpan!!
+    listener.callFailed(call, error)
+
+    assertThat(callSpan.status).isEqualTo(SpanStatus.INTERNAL_ERROR)
+    assertThat(callSpan.throwable).isSameInstanceAs(error)
+    assertThat(callSpan.getData("error_message")).isEqualTo("Connection refused")
+  }
+
   private fun verifyDelegation(
     listener: SentryOkHttpEventListener,
     originalListener: EventListener,