diff --git a/embrace-android-core/src/main/kotlin/io/embrace/android/embracesdk/internal/logs/attachments/Attachment.kt b/embrace-android-core/src/main/kotlin/io/embrace/android/embracesdk/internal/logs/attachments/Attachment.kt
index 0a5923ba46..8c76b8a376 100644
--- a/embrace-android-core/src/main/kotlin/io/embrace/android/embracesdk/internal/logs/attachments/Attachment.kt
+++ b/embrace-android-core/src/main/kotlin/io/embrace/android/embracesdk/internal/logs/attachments/Attachment.kt
@@ -21,6 +21,7 @@ sealed class Attachment(val id: String) {
     }
 
     abstract val attributes: Map<EmbraceAttributeKey, String>
+    abstract val errorCode: AttachmentErrorCode?
 
     protected fun constructAttributes(
         id: String,
@@ -42,7 +43,7 @@ sealed class Attachment(val id: String) {
 
         private val size: Long = bytes.size.toLong()
 
-        private val errorCode: AttachmentErrorCode? = when {
+        override val errorCode: AttachmentErrorCode? = when {
             !counter() -> OVER_MAX_ATTACHMENTS
             size > LIMIT_MB -> ATTACHMENT_TOO_LARGE
             else -> null
@@ -64,7 +65,7 @@ sealed class Attachment(val id: String) {
         counter: () -> Boolean,
     ) : Attachment(id) {
 
-        private val errorCode: AttachmentErrorCode? = when {
+        override val errorCode: AttachmentErrorCode? = when {
             !counter() -> OVER_MAX_ATTACHMENTS
             url.isEmpty() -> UNKNOWN
             isNotUuid() -> UNKNOWN
diff --git a/embrace-android-delivery/src/main/kotlin/io/embrace/android/embracesdk/internal/delivery/SupportedEnvelopeType.kt b/embrace-android-delivery/src/main/kotlin/io/embrace/android/embracesdk/internal/delivery/SupportedEnvelopeType.kt
index 6793422ea7..7f753468e3 100644
--- a/embrace-android-delivery/src/main/kotlin/io/embrace/android/embracesdk/internal/delivery/SupportedEnvelopeType.kt
+++ b/embrace-android-delivery/src/main/kotlin/io/embrace/android/embracesdk/internal/delivery/SupportedEnvelopeType.kt
@@ -15,7 +15,7 @@ enum class SupportedEnvelopeType(
 
     CRASH(Envelope.logEnvelopeType, "p1", Endpoint.LOGS),
     SESSION(Envelope.sessionEnvelopeType, "p3", Endpoint.SESSIONS),
-    ATTACHMENT(null, "p4", Endpoint.ATTACHMENT),
+    ATTACHMENT(null, "p4", Endpoint.ATTACHMENTS),
     LOG(Envelope.logEnvelopeType, "p5", Endpoint.LOGS),
     BLOB(Envelope.logEnvelopeType, "p7", Endpoint.LOGS);
 
diff --git a/embrace-android-delivery/src/main/kotlin/io/embrace/android/embracesdk/internal/delivery/execution/OkHttpRequestExecutionService.kt b/embrace-android-delivery/src/main/kotlin/io/embrace/android/embracesdk/internal/delivery/execution/OkHttpRequestExecutionService.kt
index 747e18ff88..56c29dfc07 100644
--- a/embrace-android-delivery/src/main/kotlin/io/embrace/android/embracesdk/internal/delivery/execution/OkHttpRequestExecutionService.kt
+++ b/embrace-android-delivery/src/main/kotlin/io/embrace/android/embracesdk/internal/delivery/execution/OkHttpRequestExecutionService.kt
@@ -41,7 +41,7 @@ class OkHttpRequestExecutionService(
         envelopeType: SupportedEnvelopeType,
         payloadType: String,
     ): ExecutionResult {
-        val multipart = envelopeType.endpoint == Endpoint.ATTACHMENT
+        val multipart = envelopeType.endpoint == Endpoint.ATTACHMENTS
         val apiRequest = envelopeType.endpoint.getApiRequestFromEndpoint(multipart)
         val request = when {
             multipart -> prepareMultipartRequest(payloadStream, apiRequest)
diff --git a/embrace-android-payload/src/main/kotlin/io/embrace/android/embracesdk/internal/comms/api/Endpoint.kt b/embrace-android-payload/src/main/kotlin/io/embrace/android/embracesdk/internal/comms/api/Endpoint.kt
index a3bf5eb020..9431b6c9a5 100644
--- a/embrace-android-payload/src/main/kotlin/io/embrace/android/embracesdk/internal/comms/api/Endpoint.kt
+++ b/embrace-android-payload/src/main/kotlin/io/embrace/android/embracesdk/internal/comms/api/Endpoint.kt
@@ -10,6 +10,6 @@ enum class Endpoint(
     LOGS("logs", "v2"),
     SESSIONS("spans", "v2"),
     CONFIG("config", "v2"),
-    ATTACHMENT("attachment", "v2"),
+    ATTACHMENTS("attachments", "v2"),
     UNKNOWN("unknown", "v1"),
 }
diff --git a/embrace-android-sdk/src/integrationTest/kotlin/io/embrace/android/embracesdk/testframework/server/FakeApiServer.kt b/embrace-android-sdk/src/integrationTest/kotlin/io/embrace/android/embracesdk/testframework/server/FakeApiServer.kt
index 7552b3c5e6..430a6fa5d2 100644
--- a/embrace-android-sdk/src/integrationTest/kotlin/io/embrace/android/embracesdk/testframework/server/FakeApiServer.kt
+++ b/embrace-android-sdk/src/integrationTest/kotlin/io/embrace/android/embracesdk/testframework/server/FakeApiServer.kt
@@ -64,7 +64,7 @@ internal class FakeApiServer(
         deliveryTracer.onServerReceivedRequest(endpoint.name)
         return when (endpoint) {
             Endpoint.LOGS, Endpoint.SESSIONS -> handleEnvelopeRequest(request, endpoint)
-            Endpoint.ATTACHMENT -> handleAttachmentRequest(request)
+            Endpoint.ATTACHMENTS -> handleAttachmentRequest(request)
 
             // IMPORTANT NOTE: this response is not used until the SDK next starts!
             Endpoint.CONFIG -> handleConfigRequest(request)
@@ -150,7 +150,7 @@ internal class FakeApiServer(
             "logs" -> Endpoint.LOGS
             "spans" -> Endpoint.SESSIONS
             "config" -> Endpoint.CONFIG
-            "attachment" -> Endpoint.ATTACHMENT
+            "attachments" -> Endpoint.ATTACHMENTS
             else -> error("Unsupported path $endpoint")
         }
     }
diff --git a/embrace-android-sdk/src/main/java/io/embrace/android/embracesdk/internal/api/delegate/LogsApiDelegate.kt b/embrace-android-sdk/src/main/java/io/embrace/android/embracesdk/internal/api/delegate/LogsApiDelegate.kt
index 97b8841c4d..de1fb06021 100644
--- a/embrace-android-sdk/src/main/java/io/embrace/android/embracesdk/internal/api/delegate/LogsApiDelegate.kt
+++ b/embrace-android-sdk/src/main/java/io/embrace/android/embracesdk/internal/api/delegate/LogsApiDelegate.kt
@@ -7,6 +7,9 @@ import io.embrace.android.embracesdk.internal.injection.ModuleInitBootstrapper
 import io.embrace.android.embracesdk.internal.injection.embraceImplInject
 import io.embrace.android.embracesdk.internal.logs.attachments.Attachment
 import io.embrace.android.embracesdk.internal.logs.attachments.Attachment.EmbraceHosted
+import io.embrace.android.embracesdk.internal.logs.attachments.AttachmentErrorCode.ATTACHMENT_TOO_LARGE
+import io.embrace.android.embracesdk.internal.logs.attachments.AttachmentErrorCode.OVER_MAX_ATTACHMENTS
+import io.embrace.android.embracesdk.internal.logs.attachments.AttachmentErrorCode.UNKNOWN
 import io.embrace.android.embracesdk.internal.payload.PushNotificationBreadcrumb
 import io.embrace.android.embracesdk.internal.serialization.truncatedStacktrace
 import io.embrace.android.embracesdk.internal.utils.getSafeStackTrace
@@ -31,6 +34,9 @@ internal class LogsApiDelegate(
     private val attachmentService by embraceImplInject(sdkCallChecker) {
         bootstrapper.logModule.attachmentService
     }
+    private val logger by embraceImplInject(sdkCallChecker) {
+        bootstrapper.initModule.logger
+    }
 
     override fun logInfo(message: String) = logMessage(message, Severity.INFO)
     override fun logWarning(message: String) = logMessage(message, Severity.WARNING)
@@ -91,6 +97,7 @@ internal class LogsApiDelegate(
         attachment: ByteArray,
     ) {
         val obj = attachmentService?.createAttachment(attachment) ?: return
+        logAttachmentErrorIfNeeded(obj)
         logMessageImpl(
             severity = severity,
             message = message,
@@ -107,6 +114,7 @@ internal class LogsApiDelegate(
         attachmentUrl: String,
     ) {
         val obj = attachmentService?.createAttachment(attachmentId, attachmentUrl) ?: return
+        logAttachmentErrorIfNeeded(obj)
         logMessageImpl(
             severity = severity,
             message = message,
@@ -115,6 +123,18 @@ internal class LogsApiDelegate(
         )
     }
 
+    private fun logAttachmentErrorIfNeeded(obj: Attachment) {
+        if (obj.errorCode != null) {
+            val msg = when (obj.errorCode) {
+                ATTACHMENT_TOO_LARGE -> "Supplied attachment exceeds 1Mb limit. This attachment will not be uploaded."
+                OVER_MAX_ATTACHMENTS -> "A maximum of 5 attachments are allowed per session. This attachment will not be uploaded."
+                UNKNOWN -> "An unknown error occurred while processing the attachment."
+                null -> null
+            } ?: return
+            logger?.logError(msg, RuntimeException(msg))
+        }
+    }
+
     override fun logException(
         throwable: Throwable,
         severity: Severity,