diff --git a/build.gradle.kts b/build.gradle.kts
index 7f16e9c..bd05ee3 100644
--- a/build.gradle.kts
+++ b/build.gradle.kts
@@ -13,6 +13,7 @@ plugins {
 	alias(libs.plugins.asciidoctor.convert) apply false
 	alias(libs.plugins.epages.restdocs.api.spec) apply false
 	alias(libs.plugins.hidetake.swagger.generator) apply false
+	alias(libs.plugins.sentry.jvm.gradle) apply false
 }
 
 allprojects {
diff --git a/docker/DockerfileDev b/docker/DockerfileDev
index 2918072..d0a13a4 100644
--- a/docker/DockerfileDev
+++ b/docker/DockerfileDev
@@ -1,9 +1,17 @@
+FROM alpine:latest AS agent-downloader
+RUN wget -O /sentry-opentelemetry-agent.jar https://get.sentry.io/sentry-opentelemetry-agent.jar
+
 FROM amazoncorretto:21
 ENV TZ="Asia/Seoul"
 
-RUN mkdir -p /service/pida
+RUN mkdir -p /service/pida /opt/sentry
+COPY --from=agent-downloader /sentry-opentelemetry-agent.jar /opt/sentry/agent.jar
 COPY pida-core/core-api/build/libs/core-api-0.0.1.jar /service/pida/core-api-0.0.1.jar
 
 EXPOSE 8080
 
-CMD java -jar -Xmx2048m /service/pida/core-api-0.0.1.jar
+CMD java \
+    -javaagent:/opt/sentry/agent.jar \
+    -Dsentry.auto.init=false \
+    -Xmx2048m \
+    -jar /service/pida/core-api-0.0.1.jar
diff --git a/docker/DockerfileProd b/docker/DockerfileProd
index 1b4301e..4b5cd08 100644
--- a/docker/DockerfileProd
+++ b/docker/DockerfileProd
@@ -1,15 +1,20 @@
+FROM alpine:latest AS agent-downloader
+RUN wget -O /sentry-opentelemetry-agent.jar https://get.sentry.io/sentry-opentelemetry-agent.jar
+
 FROM amazoncorretto:21
 ENV TZ="Asia/Seoul"
 
 ARG PROFILE
 ENV PROFILE=${PROFILE}
 
-RUN mkdir -p /service/pida
-
+RUN mkdir -p /service/pida /opt/sentry
+COPY --from=agent-downloader /sentry-opentelemetry-agent.jar /opt/sentry/agent.jar
 COPY pida-core/core-api/build/libs/core-api-0.0.1.jar /service/pida/core-api-0.0.1.jar
 
 EXPOSE 8080
 
 CMD java \
+    -javaagent:/opt/sentry/agent.jar \
+    -Dsentry.auto.init=false \
     -Dspring.profiles.active=${PROFILE} \
     -jar /service/pida/core-api-0.0.1.jar
diff --git a/gradle/libs.versions.toml b/gradle/libs.versions.toml
index 04fc4c0..3c0cb92 100644
--- a/gradle/libs.versions.toml
+++ b/gradle/libs.versions.toml
@@ -37,7 +37,8 @@ hidetake_swagger_generator = "2.18.2"
 swaggerVersion = "2.8.5"
 
 # Sentry version
-sentry = "7.3.0"
+sentry = "8.31.0"
+sentry_gradle = "6.0.0"
 
 # AWS version
 aws = "2.40.13"
@@ -79,6 +80,9 @@ ktlint = { id = "org.jlleitschuh.gradle.ktlint", version.ref = "ktlint" }
 spring_boot = { id = "org.springframework.boot", version.ref = "spring_boot" }
 spring_dependency_management = { id = "io.spring.dependency-management", version.ref = "spring_dependency_management" }
 
+# Sentry Plugin
+sentry_jvm_gradle = { id = "io.sentry.jvm.gradle", version.ref = "sentry_gradle" }
+
 # Api-Docs Plugins
 asciidoctor_convert = { id = "org.asciidoctor.jvm.convert", version.ref = "asciidoctor_convert" }
 epages_restdocs_api_spec = { id = "com.epages.restdocs-api-spec", version.ref = "epages_restdocs_api_spec" }
@@ -184,6 +188,8 @@ epages_restdocs_api_spec_restassured = { module = "com.epages:restdocs-api-spec-
 # Monitoring & Logging Libraries
 micrometer_tracing_bridge_brave = { module = "io.micrometer:micrometer-tracing-bridge-brave" }
 micrometer_registry_prometheus = { module = "io.micrometer:micrometer-registry-prometheus" }
+sentry_spring_boot_starter_jakarta = { module = "io.sentry:sentry-spring-boot-starter-jakarta", version.ref = "sentry" }
+sentry_opentelemetry_agent = { module = "io.sentry:sentry-opentelemetry-agent", version.ref = "sentry" }
 slf4j = { module = "org.slf4j:slf4j-api", version = "2.0.9" }
 
 # AWS Libraries
diff --git a/pida-core/core-api/build.gradle.kts b/pida-core/core-api/build.gradle.kts
index e6a21c5..c493761 100644
--- a/pida-core/core-api/build.gradle.kts
+++ b/pida-core/core-api/build.gradle.kts
@@ -1,3 +1,18 @@
+plugins {
+    id("io.sentry.jvm.gradle")
+}
+
+val hasSentryToken = System.getenv("SENTRY_AUTH_TOKEN") != null
+
+sentry {
+    includeSourceContext.set(hasSentryToken)
+    org.set("pida-za")
+    projectName.set("pida")
+    authToken.set(System.getenv("SENTRY_AUTH_TOKEN"))
+}
+
+val sentryAgent: Configuration by configurations.creating
+
 tasks.getByName("bootJar") {
     enabled = true
 }
@@ -6,7 +21,18 @@ tasks.getByName("jar") {
     enabled = false
 }
 
+tasks.register<Copy>("copySentryAgent") {
+    from(sentryAgent)
+    into(layout.buildDirectory.dir("agent"))
+    rename { "sentry-opentelemetry-agent.jar" }
+}
+
+tasks.named("build") {
+    dependsOn("copySentryAgent")
+}
+
 dependencies {
+    sentryAgent(libs.sentry.opentelemetry.agent)
     implementation(libs.spring.boot.starter.web)
     implementation(libs.spring.boot.starter.aop)
     implementation(libs.spring.boot.starter.validation)
diff --git a/pida-supports/monitoring/build.gradle.kts b/pida-supports/monitoring/build.gradle.kts
index 3a62eb8..b7b0142 100644
--- a/pida-supports/monitoring/build.gradle.kts
+++ b/pida-supports/monitoring/build.gradle.kts
@@ -1,4 +1,6 @@
 dependencies {
     implementation(libs.spring.boot.starter.actuator)
     implementation(libs.micrometer.registry.prometheus)
+    implementation(libs.sentry.spring.boot.starter.jakarta)
+    implementation(project(":pida-core:core-domain"))
 }
diff --git a/pida-supports/monitoring/src/main/kotlin/com/pida/monitoring/sentry/SentryFingerprintCallback.kt b/pida-supports/monitoring/src/main/kotlin/com/pida/monitoring/sentry/SentryFingerprintCallback.kt
new file mode 100644
index 0000000..706e810
--- /dev/null
+++ b/pida-supports/monitoring/src/main/kotlin/com/pida/monitoring/sentry/SentryFingerprintCallback.kt
@@ -0,0 +1,44 @@
+package com.pida.monitoring.sentry
+
+import com.pida.support.error.AuthenticationErrorException
+import com.pida.support.error.ErrorException
+import io.sentry.Hint
+import io.sentry.SentryEvent
+import io.sentry.SentryOptions
+import org.springframework.stereotype.Component
+
+@Component
+class SentryFingerprintCallback : SentryOptions.BeforeSendCallback {
+    override fun execute(
+        event: SentryEvent,
+        hint: Hint,
+    ): SentryEvent {
+        val exception = event.throwable ?: return event
+
+        val fingerprint = resolveFingerprint(exception)
+        if (fingerprint != null) {
+            event.fingerprints = fingerprint
+        }
+
+        return event
+    }
+
+    private fun resolveFingerprint(exception: Throwable): List<String>? =
+        when (exception) {
+            is ErrorException ->
+                listOf(
+                    "ErrorException",
+                    exception.errorType.kind.name,
+                    exception.errorType.name,
+                )
+
+            is AuthenticationErrorException ->
+                listOf(
+                    "AuthenticationErrorException",
+                    exception.authenticationErrorType.kind.name,
+                    exception.authenticationErrorType.name,
+                )
+
+            else -> null
+        }
+}
diff --git a/pida-supports/monitoring/src/main/resources/monitoring.yml b/pida-supports/monitoring/src/main/resources/monitoring.yml
index 4c6e2f0..f762fac 100644
--- a/pida-supports/monitoring/src/main/resources/monitoring.yml
+++ b/pida-supports/monitoring/src/main/resources/monitoring.yml
@@ -5,4 +5,21 @@ management:
         include: health, prometheus
   health:
     defaults:
-      enabled: false
\ No newline at end of file
+      enabled: false
+
+sentry:
+  dsn: ${SENTRY_DSN}
+  traces-sample-rate: 1.0
+  environment: ${SPRING_PROFILES_ACTIVE:local}
+  exception-resolver-order: -2147483648
+  logging:
+    minimum-event-level: error
+    minimum-breadcrumb-level: info
+---
+spring:
+  config:
+    activate:
+      on-profile: prod
+
+sentry:
+  traces-sample-rate: 0.1