diff --git a/statecheck/expect_known_output_value.go b/statecheck/expect_known_output_value.go
index 1cf6b69e8..64c47f819 100644
--- a/statecheck/expect_known_output_value.go
+++ b/statecheck/expect_known_output_value.go
@@ -56,7 +56,7 @@ func (e expectKnownOutputValue) CheckState(ctx context.Context, req CheckStateRe
 	}
 
 	if err := e.knownValue.CheckValue(result); err != nil {
-		resp.Error = err
+		resp.Error = fmt.Errorf("error checking value for output at path: %s, err: %s", e.outputAddress, err)
 
 		return
 	}
diff --git a/statecheck/expect_known_output_value_at_path.go b/statecheck/expect_known_output_value_at_path.go
index 7ff704b06..9fb8cc4f1 100644
--- a/statecheck/expect_known_output_value_at_path.go
+++ b/statecheck/expect_known_output_value_at_path.go
@@ -57,7 +57,7 @@ func (e expectKnownOutputValueAtPath) CheckState(ctx context.Context, req CheckS
 	}
 
 	if err := e.knownValue.CheckValue(result); err != nil {
-		resp.Error = err
+		resp.Error = fmt.Errorf("error checking value for output at path: %s.%s, err: %s", e.outputAddress, e.outputPath.String(), err)
 
 		return
 	}
diff --git a/statecheck/expect_known_output_value_at_path_test.go b/statecheck/expect_known_output_value_at_path_test.go
index 018deb31b..078daee04 100644
--- a/statecheck/expect_known_output_value_at_path_test.go
+++ b/statecheck/expect_known_output_value_at_path_test.go
@@ -1442,14 +1442,16 @@ func TestExpectKnownOutputValueAtPath_CheckState_UnknownAttributeType(t *testing
 				State: &tfjson.State{
 					Values: &tfjson.StateValues{
 						Outputs: map[string]*tfjson.StateOutput{
-							"float32_output": {
-								Value: float32(123),
+							"obj": {
+								Value: map[string]any{
+									"float32_output": float32(123),
+								},
 							},
 						},
 					},
 				},
 			},
-			expectedErr: fmt.Errorf("expected json.Number value for Int64Exact check, got: float32"),
+			expectedErr: fmt.Errorf("error checking value for output at path: obj.float32_output, err: expected json.Number value for Int64Exact check, got: float32"),
 		},
 	}
 
@@ -1459,7 +1461,7 @@ func TestExpectKnownOutputValueAtPath_CheckState_UnknownAttributeType(t *testing
 		t.Run(name, func(t *testing.T) {
 			t.Parallel()
 
-			e := statecheck.ExpectKnownOutputValueAtPath("float32_output", tfjsonpath.Path{}, testCase.knownValue)
+			e := statecheck.ExpectKnownOutputValueAtPath("obj", tfjsonpath.New("float32_output"), testCase.knownValue)
 
 			resp := statecheck.CheckStateResponse{}
 
diff --git a/statecheck/expect_known_output_value_test.go b/statecheck/expect_known_output_value_test.go
index 612891f74..b3f5e2ccf 100644
--- a/statecheck/expect_known_output_value_test.go
+++ b/statecheck/expect_known_output_value_test.go
@@ -1412,7 +1412,7 @@ func TestExpectKnownOutputValue_CheckState_UnknownAttributeType(t *testing.T) {
 					},
 				},
 			},
-			expectedErr: fmt.Errorf("expected json.Number value for Int64Exact check, got: float32"),
+			expectedErr: fmt.Errorf("error checking value for output at path: float32_output, err: expected json.Number value for Int64Exact check, got: float32"),
 		},
 	}
 
diff --git a/statecheck/expect_known_value.go b/statecheck/expect_known_value.go
index 096699cba..96662c32a 100644
--- a/statecheck/expect_known_value.go
+++ b/statecheck/expect_known_value.go
@@ -61,7 +61,7 @@ func (e expectKnownValue) CheckState(ctx context.Context, req CheckStateRequest,
 	}
 
 	if err := e.knownValue.CheckValue(result); err != nil {
-		resp.Error = err
+		resp.Error = fmt.Errorf("error checking value for attribute at path: %s.%s, err: %s", e.resourceAddress, e.attributePath.String(), err)
 	}
 }
 
diff --git a/statecheck/expect_known_value_test.go b/statecheck/expect_known_value_test.go
index e275212de..9625ec089 100644
--- a/statecheck/expect_known_value_test.go
+++ b/statecheck/expect_known_value_test.go
@@ -1294,7 +1294,7 @@ func TestExpectKnownValue_CheckState_UnknownAttributeType(t *testing.T) {
 					},
 				},
 			},
-			expectedErr: fmt.Errorf("expected json.Number value for Int64Exact check, got: float32"),
+			expectedErr: fmt.Errorf("error checking value for attribute at path: example_resource.test.attribute, err: expected json.Number value for Int64Exact check, got: float32"),
 		},
 	}