diff --git a/data-prepper-logstash-configuration/src/main/java/org/opensearch/dataprepper/logstash/mapping/AbstractLogstashPluginAttributesMapper.java b/data-prepper-logstash-configuration/src/main/java/org/opensearch/dataprepper/logstash/mapping/AbstractLogstashPluginAttributesMapper.java
index 555c30de1f..fae7e26050 100644
--- a/data-prepper-logstash-configuration/src/main/java/org/opensearch/dataprepper/logstash/mapping/AbstractLogstashPluginAttributesMapper.java
+++ b/data-prepper-logstash-configuration/src/main/java/org/opensearch/dataprepper/logstash/mapping/AbstractLogstashPluginAttributesMapper.java
@@ -37,18 +37,16 @@ public Map<String, Object> mapAttributes(final List<LogstashAttribute> logstashA
                 .filter(logstashAttribute -> !customMappedAttributeNames.contains(logstashAttribute.getAttributeName()))
                 .forEach(logstashAttribute -> {
                     final String logstashAttributeName = logstashAttribute.getAttributeName();
+                    final String dataPrepperAttributeName = mappedAttributeNames.get(logstashAttributeName);
 
                     if (mappedAttributeNames.containsKey(logstashAttributeName)) {
-                        if (mappedAttributeNames.get(logstashAttributeName).startsWith("!")) {
+                        if (dataPrepperAttributeName.startsWith("!") && logstashAttribute.getAttributeValue().getValue() instanceof Boolean) {
                             pluginSettings.put(
-                                    mappedAttributeNames.get(logstashAttributeName).substring(1),
-                                    !(Boolean) logstashAttribute.getAttributeValue().getValue()
+                                    dataPrepperAttributeName.substring(1), !(Boolean) logstashAttribute.getAttributeValue().getValue()
                             );
                         }
                         else {
-                            pluginSettings.put(
-                                    mappedAttributeNames.get(logstashAttributeName),
-                                    logstashAttribute.getAttributeValue().getValue());
+                            pluginSettings.put(dataPrepperAttributeName, logstashAttribute.getAttributeValue().getValue());
                         }
                     }
                     else {
diff --git a/data-prepper-logstash-configuration/src/main/resources/org/opensearch/dataprepper/logstash/mapping/opensearch.mapping.yaml b/data-prepper-logstash-configuration/src/main/resources/org/opensearch/dataprepper/logstash/mapping/opensearch.mapping.yaml
index c4e170efb3..5f0fec03c0 100644
--- a/data-prepper-logstash-configuration/src/main/resources/org/opensearch/dataprepper/logstash/mapping/opensearch.mapping.yaml
+++ b/data-prepper-logstash-configuration/src/main/resources/org/opensearch/dataprepper/logstash/mapping/opensearch.mapping.yaml
@@ -4,4 +4,4 @@ mappedAttributeNames:
   user: username
   password: password
   index: index
-  ssl_certificate_verification: !insecure
\ No newline at end of file
+  ssl_certificate_verification: "!insecure"
\ No newline at end of file
diff --git a/data-prepper-logstash-configuration/src/test/java/org/opensearch/dataprepper/logstash/mapping/DefaultLogstashPluginAttributesMapperTest.java b/data-prepper-logstash-configuration/src/test/java/org/opensearch/dataprepper/logstash/mapping/DefaultLogstashPluginAttributesMapperTest.java
index 9fbd974b9d..bf0619dd39 100644
--- a/data-prepper-logstash-configuration/src/test/java/org/opensearch/dataprepper/logstash/mapping/DefaultLogstashPluginAttributesMapperTest.java
+++ b/data-prepper-logstash-configuration/src/test/java/org/opensearch/dataprepper/logstash/mapping/DefaultLogstashPluginAttributesMapperTest.java
@@ -7,6 +7,8 @@
 
 import org.junit.jupiter.api.BeforeEach;
 import org.junit.jupiter.api.Test;
+import org.junit.jupiter.params.ParameterizedTest;
+import org.junit.jupiter.params.provider.ValueSource;
 import org.opensearch.dataprepper.logstash.model.LogstashAttribute;
 import org.opensearch.dataprepper.logstash.model.LogstashAttributeValue;
 
@@ -116,19 +118,18 @@ void mapAttributes_sets_additional_attributes_to_those_values() {
         assertThat(actualPluginSettings.get(additionalAttributeName), equalTo(additionalAttributeValue));
     }
 
-    @Test
-    void mapAttributes_with_negation_expression_negates_boolean_value() {
+    @ParameterizedTest
+    @ValueSource(booleans = { true, false } )
+    void mapAttributes_with_negation_expression_negates_boolean_value(boolean inputValue) {
         final String dataPrepperAttribute = "!".concat(UUID.randomUUID().toString());
-        boolean value = true;
 
-        when(logstashAttributeValue.getValue()).thenReturn(value);
+        when(logstashAttributeValue.getValue()).thenReturn(inputValue);
         when(mappings.getMappedAttributeNames()).thenReturn(Collections.singletonMap(logstashAttributeName, dataPrepperAttribute));
 
-        final Map<String, Object> actualPluginSettings =
-                createObjectUnderTest().mapAttributes(logstashAttributes, mappings);
+        final Map<String, Object> actualPluginSettings = createObjectUnderTest().mapAttributes(logstashAttributes, mappings);
 
         assertThat(actualPluginSettings, notNullValue());
         assertThat(actualPluginSettings.size(), equalTo(1));
-        assertThat(actualPluginSettings.get(dataPrepperAttribute.substring(1)), equalTo(!value));
+        assertThat(actualPluginSettings.get(dataPrepperAttribute.substring(1)), equalTo(!inputValue));
     }
 }
\ No newline at end of file
diff --git a/data-prepper-logstash-configuration/src/test/resources/org/opensearch/dataprepper/logstash/log-ingest-to-logstash-opensearch-insecure.expected.yaml b/data-prepper-logstash-configuration/src/test/resources/org/opensearch/dataprepper/logstash/log-ingest-to-logstash-opensearch-insecure.expected.yaml
new file mode 100644
index 0000000000..4050cab6bb
--- /dev/null
+++ b/data-prepper-logstash-configuration/src/test/resources/org/opensearch/dataprepper/logstash/log-ingest-to-logstash-opensearch-insecure.expected.yaml
@@ -0,0 +1,18 @@
+logstash-converted-pipeline:
+  source:
+    http:
+      max_connection_count: 500
+      request_timeout: 10000
+  processor:
+    - grok:
+        match:
+          log:
+            - "%{COMBINEDAPACHELOG}"
+  sink:
+    - opensearch:
+        hosts:
+          - "fakedomain.us-east-1.es.amazonaws.com"
+        username: "myuser"
+        password: "mypassword"
+        index: "my-index"
+        insecure: true
diff --git a/data-prepper-logstash-configuration/src/test/resources/org/opensearch/dataprepper/logstash/log-ingest-to-logstash-opensearch.conf b/data-prepper-logstash-configuration/src/test/resources/org/opensearch/dataprepper/logstash/log-ingest-to-logstash-opensearch.conf
new file mode 100644
index 0000000000..acad6f6cd3
--- /dev/null
+++ b/data-prepper-logstash-configuration/src/test/resources/org/opensearch/dataprepper/logstash/log-ingest-to-logstash-opensearch.conf
@@ -0,0 +1,18 @@
+input {
+    http {
+    }
+}
+filter {
+    grok {
+        match => {"log" => "%{COMBINEDAPACHELOG}"}
+    }
+}
+output {
+    opensearch {
+        hosts => ["fakedomain.us-east-1.es.amazonaws.com"]
+        user => myuser
+        password => mypassword
+        index => "my-index"
+        ssl_certificate_verification => true
+    }
+}
\ No newline at end of file
diff --git a/data-prepper-logstash-configuration/src/test/resources/org/opensearch/dataprepper/logstash/log-ingest-to-logstash-opensearch.expected.yaml b/data-prepper-logstash-configuration/src/test/resources/org/opensearch/dataprepper/logstash/log-ingest-to-logstash-opensearch.expected.yaml
new file mode 100644
index 0000000000..618dddeaf0
--- /dev/null
+++ b/data-prepper-logstash-configuration/src/test/resources/org/opensearch/dataprepper/logstash/log-ingest-to-logstash-opensearch.expected.yaml
@@ -0,0 +1,18 @@
+logstash-converted-pipeline:
+  source:
+    http:
+      max_connection_count: 500
+      request_timeout: 10000
+  processor:
+    - grok:
+        match:
+          log:
+            - "%{COMBINEDAPACHELOG}"
+  sink:
+    - opensearch:
+        hosts:
+          - "fakedomain.us-east-1.es.amazonaws.com"
+        username: "myuser"
+        password: "mypassword"
+        index: "my-index"
+        insecure: false
diff --git a/data-prepper-logstash-configuration/src/test/resources/org/opensearch/dataprepper/logstash/log-ingest-to-logtstash-opensearch-insecure.conf b/data-prepper-logstash-configuration/src/test/resources/org/opensearch/dataprepper/logstash/log-ingest-to-logtstash-opensearch-insecure.conf
new file mode 100644
index 0000000000..4c08eb5da0
--- /dev/null
+++ b/data-prepper-logstash-configuration/src/test/resources/org/opensearch/dataprepper/logstash/log-ingest-to-logtstash-opensearch-insecure.conf
@@ -0,0 +1,18 @@
+input {
+    http {
+    }
+}
+filter {
+    grok {
+        match => {"log" => "%{COMBINEDAPACHELOG}"}
+    }
+}
+output {
+    opensearch {
+        hosts => ["fakedomain.us-east-1.es.amazonaws.com"]
+        user => myuser
+        password => mypassword
+        index => "my-index"
+        ssl_certificate_verification => false
+    }
+}
\ No newline at end of file