diff --git a/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/Assertion.java b/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/Assertion.java
index b9cbaacdf8873..bf8f41dca33fd 100644
--- a/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/Assertion.java
+++ b/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/Assertion.java
@@ -37,6 +37,8 @@
 import java.io.IOException;
 import java.util.Map;
 
+import static org.junit.Assert.fail;
+
 /**
  * Base class for executable sections that hold assertions
  */
@@ -73,10 +75,49 @@ protected final Object resolveExpectedValue(ClientYamlTestExecutionContext execu
     }
 
     protected final Object getActualValue(ClientYamlTestExecutionContext executionContext) throws IOException {
+        Object actualValue;
         if (executionContext.stash().containsStashedValue(field)) {
-            return executionContext.stash().getValue(field);
+            actualValue = executionContext.stash().getValue(field);
+        } else {
+            actualValue = executionContext.response(field);
+        }
+        // Expected/actual values have compatible types, or they're not expected to have the same. Can just return.
+        if (actualValue == null || expectedValue.getClass().isAssignableFrom(actualValue.getClass()) || !expectedAndActualHaveSameType()) {
+            return actualValue;
+        }
+        if (actualValue instanceof Number && expectedValue instanceof Number) {
+            if (expectedValue instanceof Float) {
+                return Float.parseFloat(actualValue.toString());
+            } else if (expectedValue instanceof Double) {
+                return Double.parseDouble(actualValue.toString());
+            } else if (expectedValue instanceof Integer) {
+                return Integer.parseInt(actualValue.toString());
+            } else if (expectedValue instanceof Long) {
+                return Long.parseLong(actualValue.toString());
+            }
         }
-        return executionContext.response(field);
+        // Force a class cast exception here, so developers can flesh out the above logic as needed.
+        try {
+            expectedValue.getClass().cast(actualValue);
+        } catch (ClassCastException e) {
+            fail(
+                "Type mismatch: Expected value ("
+                    + expectedValue
+                    + ") has type "
+                    + expectedValue.getClass()
+                    + ". "
+                    + "Actual value ("
+                    + actualValue
+                    + ") has type "
+                    + actualValue.getClass()
+                    + "."
+            );
+        }
+        return actualValue;
+    }
+
+    protected boolean expectedAndActualHaveSameType() {
+        return true;
     }
 
     @Override
diff --git a/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/ContainsAssertion.java b/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/ContainsAssertion.java
index 8012b90b1b04f..e1ea8313d9546 100644
--- a/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/ContainsAssertion.java
+++ b/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/ContainsAssertion.java
@@ -91,4 +91,9 @@ protected void doAssert(Object actualValue, Object expectedValue) {
             fail("'contains' only supports checking an object against a list of objects");
         }
     }
+
+    @Override
+    protected boolean expectedAndActualHaveSameType() {
+        return false;
+    }
 }
diff --git a/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/IsFalseAssertion.java b/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/IsFalseAssertion.java
index 999486ad04455..0908a8d3c13d3 100644
--- a/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/IsFalseAssertion.java
+++ b/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/IsFalseAssertion.java
@@ -75,4 +75,9 @@ protected void doAssert(Object actualValue, Object expectedValue) {
     private String errorMessage() {
         return "field [" + getField() + "] has a true value but it shouldn't";
     }
+
+    @Override
+    protected boolean expectedAndActualHaveSameType() {
+        return false;
+    }
 }
diff --git a/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/IsTrueAssertion.java b/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/IsTrueAssertion.java
index bf5822406f014..68e154e8db778 100644
--- a/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/IsTrueAssertion.java
+++ b/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/IsTrueAssertion.java
@@ -75,4 +75,9 @@ protected void doAssert(Object actualValue, Object expectedValue) {
     private String errorMessage() {
         return "field [" + getField() + "] doesn't have a true value";
     }
+
+    @Override
+    protected boolean expectedAndActualHaveSameType() {
+        return false;
+    }
 }
diff --git a/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/LengthAssertion.java b/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/LengthAssertion.java
index fd7d8d632cc1e..dfbd6580f4403 100644
--- a/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/LengthAssertion.java
+++ b/test/framework/src/main/java/org/opensearch/test/rest/yaml/section/LengthAssertion.java
@@ -97,4 +97,9 @@ protected void doAssert(Object actualValue, Object expectedValue) {
     private String errorMessage() {
         return "field [" + getField() + "] doesn't have length [" + getExpectedValue() + "]";
     }
+
+    @Override
+    protected boolean expectedAndActualHaveSameType() {
+        return false; // Expected value is a number, while actual will some type with a length.
+    }
 }