diff --git a/orca-clouddriver/orca-clouddriver.gradle b/orca-clouddriver/orca-clouddriver.gradle
index 8bc29adf0a6..05c3b29cc42 100644
--- a/orca-clouddriver/orca-clouddriver.gradle
+++ b/orca-clouddriver/orca-clouddriver.gradle
@@ -59,6 +59,7 @@ dependencies {
   testImplementation("io.strikt:strikt-core")
   testImplementation("io.mockk:mockk")
   testImplementation("ru.lanwen.wiremock:wiremock-junit5:1.3.1")
+  testImplementation("org.mockito:mockito-inline")
 
   testCompileOnly("org.projectlombok:lombok")
   testAnnotationProcessor("org.projectlombok:lombok")
diff --git a/orca-clouddriver/src/test/groovy/com/netflix/spinnaker/orca/clouddriver/tasks/monitoreddeploy/EvaluateDeploymentHealthTaskSpec.groovy b/orca-clouddriver/src/test/groovy/com/netflix/spinnaker/orca/clouddriver/tasks/monitoreddeploy/EvaluateDeploymentHealthTaskSpec.groovy
index b26591e1d72..098678ae339 100644
--- a/orca-clouddriver/src/test/groovy/com/netflix/spinnaker/orca/clouddriver/tasks/monitoreddeploy/EvaluateDeploymentHealthTaskSpec.groovy
+++ b/orca-clouddriver/src/test/groovy/com/netflix/spinnaker/orca/clouddriver/tasks/monitoreddeploy/EvaluateDeploymentHealthTaskSpec.groovy
@@ -16,10 +16,12 @@
 
 package com.netflix.spinnaker.orca.clouddriver.tasks.monitoreddeploy
 
+import com.fasterxml.jackson.databind.ObjectMapper
 import com.netflix.spectator.api.NoopRegistry
 import com.netflix.spinnaker.config.DeploymentMonitorDefinition
 import com.netflix.spinnaker.orca.api.pipeline.models.ExecutionStatus
 import com.netflix.spinnaker.orca.api.pipeline.TaskResult
+import com.netflix.spinnaker.orca.clouddriver.MortServiceSpec
 import com.netflix.spinnaker.orca.deploymentmonitor.DeploymentMonitorService
 import com.netflix.spinnaker.orca.deploymentmonitor.models.DeploymentMonitorStageConfig
 import com.netflix.spinnaker.orca.deploymentmonitor.models.DeploymentStep
@@ -28,9 +30,13 @@ import com.netflix.spinnaker.orca.deploymentmonitor.models.MonitoredDeployIntern
 import com.netflix.spinnaker.orca.pipeline.model.PipelineExecutionImpl
 import com.netflix.spinnaker.orca.pipeline.model.StageExecutionImpl
 import retrofit.RetrofitError
+import retrofit.client.Response
+import retrofit.converter.ConversionException
+import retrofit.converter.JacksonConverter
 import spock.lang.Specification
 import com.netflix.spinnaker.orca.deploymentmonitor.DeploymentMonitorServiceProvider
 import spock.lang.Unroll
+import org.springframework.http.HttpStatus
 
 import java.time.Instant
 import java.util.concurrent.TimeUnit
@@ -41,7 +47,7 @@ class EvaluateDeploymentHealthTaskSpec extends Specification {
   PipelineExecutionImpl pipe = pipeline {
   }
 
-  def "should retry retrofit errors"() {
+  def "should handle retrofit network error and return the task status depending on the scenarios"() {
     given:
     def monitorServiceStub = Stub(DeploymentMonitorService) {
       evaluateHealth(_) >> {
@@ -198,6 +204,202 @@ class EvaluateDeploymentHealthTaskSpec extends Specification {
     false              | null             || ExecutionStatus.FAILED_CONTINUE
   }
 
+  def "should handle retrofit http error and return the task status depending on the scenarios"() {
+
+    def converter = new JacksonConverter(new ObjectMapper())
+
+    Response response =
+      new Response(
+          "/deployment/evaluateHealth",
+          HttpStatus.BAD_REQUEST.value(),
+          "bad-request",
+          Collections.emptyList(),
+          new MortServiceSpec.MockTypedInput(converter, [
+              accountName: "account",
+              description: "simple description",
+              name: "sg1",
+              region: "region",
+              type: "openstack"
+          ]))
+
+  given:
+  def monitorServiceStub = Stub(DeploymentMonitorService) {
+    evaluateHealth(_) >> {
+      throw RetrofitError.httpError("https://foo.com/deployment/evaluateHealth", response, converter, null)
+    }
+  }
+
+  def serviceProviderStub = getServiceProviderStub(monitorServiceStub)
+
+  def task = new EvaluateDeploymentHealthTask(serviceProviderStub, new NoopRegistry())
+
+  MonitoredDeployInternalStageData stageData = new MonitoredDeployInternalStageData()
+  stageData.deploymentMonitor = new DeploymentMonitorStageConfig()
+  stageData.deploymentMonitor.id = "LogMonitorId"
+
+  def stage = new StageExecutionImpl(pipe, "evaluateDeploymentHealth", stageData.toContextMap() + [application: pipe.application])
+  stage.startTime = Instant.now().toEpochMilli()
+
+  when: 'we can still retry'
+  TaskResult result = task.execute(stage)
+
+  then: 'should retry'
+  result.status == ExecutionStatus.RUNNING
+      result.context.deployMonitorHttpRetryCount == 1
+
+    when: 'we ran out of retries'
+    stage.context.deployMonitorHttpRetryCount = MonitoredDeployBaseTask.MAX_RETRY_COUNT
+    result = task.execute(stage)
+
+    then: 'should terminate'
+    result.status == ExecutionStatus.TERMINAL
+
+    when: 'we ran out of retries and failOnError = false'
+    serviceProviderStub = getServiceProviderStub(monitorServiceStub, {DeploymentMonitorDefinition dm -> dm.failOnError = false})
+    task = new EvaluateDeploymentHealthTask(serviceProviderStub, new NoopRegistry())
+    result = task.execute(stage)
+
+    then: 'should return fail_continue'
+    result.status == ExecutionStatus.FAILED_CONTINUE
+
+    when: 'we ran out of retries and failOnError = false but there is a stage override for failOnError=true'
+    stageData.deploymentMonitor.failOnErrorOverride = true
+    stage = new StageExecutionImpl(pipe, "evaluateDeploymentHealth", stageData.toContextMap() + [
+        application: pipe.application,
+        deployMonitorHttpRetryCount: MonitoredDeployBaseTask.MAX_RETRY_COUNT
+    ])
+    stage.startTime = Instant.now().toEpochMilli()
+    result = task.execute(stage)
+
+    then: 'should terminate'
+    result.status == ExecutionStatus.TERMINAL
+}
+
+  def "should handle retrofit conversion error and return the task status depending on the scenarios"() {
+    def converter = new JacksonConverter(new ObjectMapper())
+
+    Response response =
+        new Response(
+            "/deployment/evaluateHealth",
+            HttpStatus.BAD_REQUEST.value(),
+            "bad-request",
+            Collections.emptyList(),
+            new MortServiceSpec.MockTypedInput(converter, [
+                accountName: "account",
+                description: "simple description",
+                name: "sg1",
+                region: "region",
+                type: "openstack"
+            ]))
+
+    given:
+    def monitorServiceStub = Stub(DeploymentMonitorService) {
+      evaluateHealth(_) >> {
+        throw RetrofitError.conversionError("https://foo.com/deployment/evaluateHealth", response, converter, null, new ConversionException("Failed to parse/convert the error response body"))
+      }
+    }
+
+    def serviceProviderStub = getServiceProviderStub(monitorServiceStub)
+
+    def task = new EvaluateDeploymentHealthTask(serviceProviderStub, new NoopRegistry())
+
+    MonitoredDeployInternalStageData stageData = new MonitoredDeployInternalStageData()
+    stageData.deploymentMonitor = new DeploymentMonitorStageConfig()
+    stageData.deploymentMonitor.id = "LogMonitorId"
+
+    def stage = new StageExecutionImpl(pipe, "evaluateDeploymentHealth", stageData.toContextMap() + [application: pipe.application])
+    stage.startTime = Instant.now().toEpochMilli()
+
+    when: 'we can still retry'
+    TaskResult result = task.execute(stage)
+
+    then: 'should retry'
+    result.status == ExecutionStatus.RUNNING
+    result.context.deployMonitorHttpRetryCount == 1
+
+    when: 'we ran out of retries'
+    stage.context.deployMonitorHttpRetryCount = MonitoredDeployBaseTask.MAX_RETRY_COUNT
+    result = task.execute(stage)
+
+    then: 'should terminate'
+    result.status == ExecutionStatus.TERMINAL
+
+    when: 'we ran out of retries and failOnError = false'
+    serviceProviderStub = getServiceProviderStub(monitorServiceStub, {DeploymentMonitorDefinition dm -> dm.failOnError = false})
+    task = new EvaluateDeploymentHealthTask(serviceProviderStub, new NoopRegistry())
+    result = task.execute(stage)
+
+    then: 'should return fail_continue'
+    result.status == ExecutionStatus.FAILED_CONTINUE
+
+    when: 'we ran out of retries and failOnError = false but there is a stage override for failOnError=true'
+    stageData.deploymentMonitor.failOnErrorOverride = true
+    stage = new StageExecutionImpl(pipe, "evaluateDeploymentHealth", stageData.toContextMap() + [
+        application: pipe.application,
+        deployMonitorHttpRetryCount: MonitoredDeployBaseTask.MAX_RETRY_COUNT
+    ])
+    stage.startTime = Instant.now().toEpochMilli()
+    result = task.execute(stage)
+
+    then: 'should terminate'
+    result.status == ExecutionStatus.TERMINAL
+  }
+
+  def "should handle retrofit unexpected error and return the task status depending on the scenarios"() {
+
+    given:
+    def monitorServiceStub = Stub(DeploymentMonitorService) {
+      evaluateHealth(_) >> {
+        throw RetrofitError.unexpectedError("url", new IOException())
+      }
+    }
+
+    def serviceProviderStub = getServiceProviderStub(monitorServiceStub)
+
+    def task = new EvaluateDeploymentHealthTask(serviceProviderStub, new NoopRegistry())
+
+    MonitoredDeployInternalStageData stageData = new MonitoredDeployInternalStageData()
+    stageData.deploymentMonitor = new DeploymentMonitorStageConfig()
+    stageData.deploymentMonitor.id = "LogMonitorId"
+
+    def stage = new StageExecutionImpl(pipe, "evaluateDeploymentHealth", stageData.toContextMap() + [application: pipe.application])
+    stage.startTime = Instant.now().toEpochMilli()
+
+    when: 'we can still retry'
+    TaskResult result = task.execute(stage)
+
+    then: 'should retry'
+    result.status == ExecutionStatus.RUNNING
+    result.context.deployMonitorHttpRetryCount == 1
+
+    when: 'we ran out of retries'
+    stage.context.deployMonitorHttpRetryCount = MonitoredDeployBaseTask.MAX_RETRY_COUNT
+    result = task.execute(stage)
+
+    then: 'should terminate'
+    result.status == ExecutionStatus.TERMINAL
+
+    when: 'we ran out of retries and failOnError = false'
+    serviceProviderStub = getServiceProviderStub(monitorServiceStub, {DeploymentMonitorDefinition dm -> dm.failOnError = false})
+    task = new EvaluateDeploymentHealthTask(serviceProviderStub, new NoopRegistry())
+    result = task.execute(stage)
+
+    then: 'should return fail_continue'
+    result.status == ExecutionStatus.FAILED_CONTINUE
+
+    when: 'we ran out of retries and failOnError = false but there is a stage override for failOnError=true'
+    stageData.deploymentMonitor.failOnErrorOverride = true
+    stage = new StageExecutionImpl(pipe, "evaluateDeploymentHealth", stageData.toContextMap() + [
+        application: pipe.application,
+        deployMonitorHttpRetryCount: MonitoredDeployBaseTask.MAX_RETRY_COUNT
+    ])
+    stage.startTime = Instant.now().toEpochMilli()
+    result = task.execute(stage)
+
+    then: 'should terminate'
+    result.status == ExecutionStatus.TERMINAL
+  }
+
   private getServiceProviderStub(monitorServiceStub) {
     return getServiceProviderStub(monitorServiceStub, {})
   }
diff --git a/orca-clouddriver/src/test/java/com/netflix/spinnaker/orca/clouddriver/tasks/monitoreddeploy/MonitoredDeployBaseTaskTest.java b/orca-clouddriver/src/test/java/com/netflix/spinnaker/orca/clouddriver/tasks/monitoreddeploy/MonitoredDeployBaseTaskTest.java
index 784241c377d..f798b097c5d 100644
--- a/orca-clouddriver/src/test/java/com/netflix/spinnaker/orca/clouddriver/tasks/monitoreddeploy/MonitoredDeployBaseTaskTest.java
+++ b/orca-clouddriver/src/test/java/com/netflix/spinnaker/orca/clouddriver/tasks/monitoreddeploy/MonitoredDeployBaseTaskTest.java
@@ -19,6 +19,7 @@
 import static org.assertj.core.api.Assertions.assertThat;
 
 import com.fasterxml.jackson.databind.ObjectMapper;
+import com.google.common.io.CharStreams;
 import com.netflix.spectator.api.NoopRegistry;
 import com.netflix.spinnaker.config.DeploymentMonitorDefinition;
 import com.netflix.spinnaker.orca.deploymentmonitor.DeploymentMonitorServiceProvider;
@@ -26,10 +27,14 @@
 import java.io.ByteArrayOutputStream;
 import java.io.IOException;
 import java.io.InputStream;
+import java.io.InputStreamReader;
+import java.nio.charset.StandardCharsets;
 import java.util.ArrayList;
+import java.util.Collections;
 import java.util.HashMap;
 import org.junit.jupiter.api.BeforeEach;
 import org.junit.jupiter.api.Test;
+import org.mockito.Mockito;
 import org.springframework.http.HttpHeaders;
 import org.springframework.http.HttpStatus;
 import org.springframework.http.MediaType;
@@ -168,6 +173,99 @@ void shouldReturnDefaultLogMsgWhenUnexpectedErrorHasOccurred() {
     assertThat(logMessageOnUnexpectedError).isEqualTo("<NO RESPONSE>");
   }
 
+  @Test
+  void shouldReturnEmptyHttpErrorDetailsWhenExceptionThrownWhileReadingHttpStatus() {
+
+    var converter = new JacksonConverter(objectMapper);
+    var responseBody = new HashMap<String, String>();
+
+    responseBody.put("error", "400 - Bad request, application name cannot be empty");
+
+    Response response =
+        Mockito.spy(
+            new Response(
+                "/deployment/evaluateHealth",
+                HttpStatus.BAD_REQUEST.value(),
+                HttpStatus.BAD_REQUEST.name(),
+                Collections.emptyList(),
+                new MockTypedInput(converter, responseBody)));
+
+    Mockito.when(response.getStatus()).thenThrow(IllegalArgumentException.class);
+
+    String logMessageOnHttpError = monitoredDeployBaseTask.getRetrofitLogMessage(response);
+
+    String status = "";
+    String body = "";
+    String headers = "";
+
+    assertThat(logMessageOnHttpError)
+        .isEqualTo(
+            String.format("status: %s\nheaders: %s\nresponse body: %s", status, headers, body));
+  }
+
+  @Test
+  void shouldReturnOnlyStatusWhenExceptionThrownWhileParsingHttpErrorBody() {
+
+    var converter = new JacksonConverter(objectMapper);
+    var responseBody = new HashMap<String, String>();
+
+    responseBody.put("error", "400 - Bad request, application name cannot be empty");
+
+    Response response =
+        Mockito.spy(
+            new Response(
+                "/deployment/evaluateHealth",
+                HttpStatus.BAD_REQUEST.value(),
+                HttpStatus.BAD_REQUEST.name(),
+                Collections.emptyList(),
+                new MockTypedInput(converter, responseBody)));
+
+    Mockito.when(response.getBody()).thenThrow(IllegalArgumentException.class);
+
+    String logMessageOnHttpError = monitoredDeployBaseTask.getRetrofitLogMessage(response);
+
+    String status = String.format("%d (%s)", response.getStatus(), response.getReason());
+    String body = "";
+    String headers = "";
+
+    assertThat(logMessageOnHttpError)
+        .isEqualTo(
+            String.format("status: %s\nheaders: %s\nresponse body: %s", status, headers, body));
+  }
+
+  @Test
+  void shouldReturnOnlyStatusAndBodyWhenExceptionThrownWhileReadingHttpHeaders()
+      throws IOException {
+
+    var converter = new JacksonConverter(objectMapper);
+    var responseBody = new HashMap<String, String>();
+
+    responseBody.put("error", "400 - Bad request, application name cannot be empty");
+
+    Response response =
+        Mockito.spy(
+            new Response(
+                "/deployment/evaluateHealth",
+                HttpStatus.BAD_REQUEST.value(),
+                HttpStatus.BAD_REQUEST.name(),
+                Collections.emptyList(),
+                new MockTypedInput(converter, responseBody)));
+
+    Mockito.when(response.getHeaders()).thenThrow(IllegalArgumentException.class);
+
+    String logMessageOnHttpError = monitoredDeployBaseTask.getRetrofitLogMessage(response);
+
+    String status = String.format("%d (%s)", response.getStatus(), response.getReason());
+    String body =
+        CharStreams.toString(
+            new InputStreamReader(response.getBody().in(), StandardCharsets.UTF_8));
+    String headers = "";
+
+    assertThat(logMessageOnHttpError)
+        .isEqualTo(
+            String.format("status: %s\nheaders: %s\nresponse body: %s", status, headers, body));
+  }
+
   static class MockTypedInput implements TypedInput {
     private final Converter converter;
     private final Object body;