diff --git a/CHANGELOG.md b/CHANGELOG.md
index 387a9db..54536c4 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,6 +4,10 @@ All notable changes to this project will be documented in this file.
 The format is based on [Keep a Changelog](http://keepachangelog.com/en/1.0.0/)
 and this project adheres to [Semantic Versioning](http://semver.org/spec/v2.0.0.html).
 
+## [Unreleased]
+### Fixed
+- Fix failed message expiration check.
+
 ## [1.1.0] - 2023-01-16
 
 ## [1.1.0-alpha.0] - 2022-12-15
diff --git a/DeviceSDKAndroid/src/main/java/org/astarteplatform/devicesdk/android/AstarteAndroidFailedMessage.java b/DeviceSDKAndroid/src/main/java/org/astarteplatform/devicesdk/android/AstarteAndroidFailedMessage.java
index 4429dbe..1019c4f 100644
--- a/DeviceSDKAndroid/src/main/java/org/astarteplatform/devicesdk/android/AstarteAndroidFailedMessage.java
+++ b/DeviceSDKAndroid/src/main/java/org/astarteplatform/devicesdk/android/AstarteAndroidFailedMessage.java
@@ -4,6 +4,7 @@
 import androidx.room.ColumnInfo;
 import androidx.room.Entity;
 import androidx.room.PrimaryKey;
+import java.util.concurrent.TimeUnit;
 import org.astarteplatform.devicesdk.transport.AstarteFailedMessage;
 
 @Entity(tableName = "failed_messages")
@@ -30,7 +31,7 @@ public AstarteAndroidFailedMessage(String topic, byte[] payload, int qos) {
   }
 
   public AstarteAndroidFailedMessage(String topic, byte[] payload, int qos, int relativeExpiry) {
-    this.absoluteExpiry = System.currentTimeMillis() + relativeExpiry;
+    this.absoluteExpiry = System.currentTimeMillis() + TimeUnit.SECONDS.toMillis(relativeExpiry);
     this.topic = topic;
     this.payload = payload;
     this.qos = qos;
@@ -61,7 +62,11 @@ public void setAbsoluteExpiry(long absoluteExpiry) {
 
   @Override
   public boolean isExpired() {
-    return absoluteExpiry > System.currentTimeMillis();
+    if (absoluteExpiry <= 0) {
+      return false;
+    }
+
+    return absoluteExpiry < System.currentTimeMillis();
   }
 
   public long getStorageId() {
diff --git a/DeviceSDKGeneric/src/main/java/org/astarteplatform/devicesdk/generic/AstarteGenericFailedMessage.java b/DeviceSDKGeneric/src/main/java/org/astarteplatform/devicesdk/generic/AstarteGenericFailedMessage.java
index cbf78a2..e14643a 100644
--- a/DeviceSDKGeneric/src/main/java/org/astarteplatform/devicesdk/generic/AstarteGenericFailedMessage.java
+++ b/DeviceSDKGeneric/src/main/java/org/astarteplatform/devicesdk/generic/AstarteGenericFailedMessage.java
@@ -3,6 +3,7 @@
 import com.j256.ormlite.field.DataType;
 import com.j256.ormlite.field.DatabaseField;
 import com.j256.ormlite.table.DatabaseTable;
+import java.util.concurrent.TimeUnit;
 import org.astarteplatform.devicesdk.transport.AstarteFailedMessage;
 
 @DatabaseTable(tableName = "failed_messages")
@@ -34,7 +35,7 @@ public AstarteGenericFailedMessage(String topic, byte[] payload, int qos) {
   }
 
   public AstarteGenericFailedMessage(String topic, byte[] payload, int qos, int relativeExpiry) {
-    this.absoluteExpiry = System.currentTimeMillis() + relativeExpiry;
+    this.absoluteExpiry = System.currentTimeMillis() + TimeUnit.SECONDS.toMillis(relativeExpiry);
     this.topic = topic;
     this.payload = payload;
     this.qos = qos;
@@ -57,7 +58,11 @@ public int getQos() {
 
   @Override
   public boolean isExpired() {
-    return absoluteExpiry > System.currentTimeMillis();
+    if (absoluteExpiry <= 0) {
+      return false;
+    }
+
+    return absoluteExpiry < System.currentTimeMillis();
   }
 
   public long getStorageId() {