diff --git a/private/bufpkg/bufconfig/buf_gen_yaml_file.go b/private/bufpkg/bufconfig/buf_gen_yaml_file.go
index 261fd015d9..7184a2923a 100644
--- a/private/bufpkg/bufconfig/buf_gen_yaml_file.go
+++ b/private/bufpkg/bufconfig/buf_gen_yaml_file.go
@@ -17,7 +17,6 @@ package bufconfig
 import (
 	"context"
 	"encoding/json"
-	"fmt"
 	"io"
 
 	"buf.build/go/standard/xslices"
@@ -179,7 +178,7 @@ func readBufGenYAMLFile(
 	case FileVersionV1Beta1:
 		var externalGenYAMLFile externalBufGenYAMLFileV1Beta1
 		if err := getUnmarshalStrict(allowJSON)(data, &externalGenYAMLFile); err != nil {
-			return nil, fmt.Errorf("invalid as version %v: %w", fileVersion, err)
+			return nil, err
 		}
 		generateConfig, err := newGenerateConfigFromExternalFileV1Beta1(externalGenYAMLFile)
 		if err != nil {
@@ -194,7 +193,7 @@ func readBufGenYAMLFile(
 	case FileVersionV1:
 		var externalGenYAMLFile externalBufGenYAMLFileV1
 		if err := getUnmarshalStrict(allowJSON)(data, &externalGenYAMLFile); err != nil {
-			return nil, fmt.Errorf("invalid as version %v: %w", fileVersion, err)
+			return nil, err
 		}
 		generateConfig, err := newGenerateConfigFromExternalFileV1(externalGenYAMLFile)
 		if err != nil {
@@ -209,7 +208,7 @@ func readBufGenYAMLFile(
 	case FileVersionV2:
 		var externalGenYAMLFile externalBufGenYAMLFileV2
 		if err := getUnmarshalStrict(allowJSON)(data, &externalGenYAMLFile); err != nil {
-			return nil, fmt.Errorf("invalid as version %v: %w", fileVersion, err)
+			return nil, err
 		}
 		generateConfig, err := newGenerateConfigFromExternalFileV2(externalGenYAMLFile)
 		if err != nil {
diff --git a/private/bufpkg/bufconfig/buf_lock_file.go b/private/bufpkg/bufconfig/buf_lock_file.go
index 152b19e047..f75ecca337 100644
--- a/private/bufpkg/bufconfig/buf_lock_file.go
+++ b/private/bufpkg/bufconfig/buf_lock_file.go
@@ -353,7 +353,7 @@ func readBufLockFile(
 	case FileVersionV1Beta1, FileVersionV1:
 		var externalBufLockFile externalBufLockFileV1Beta1V1
 		if err := getUnmarshalStrict(allowJSON)(data, &externalBufLockFile); err != nil {
-			return nil, fmt.Errorf("invalid as version %v: %w", fileVersion, err)
+			return nil, err
 		}
 		depModuleKeys := make([]bufmodule.ModuleKey, len(externalBufLockFile.Deps))
 		for i, dep := range externalBufLockFile.Deps {
@@ -406,7 +406,7 @@ func readBufLockFile(
 	case FileVersionV2:
 		var externalBufLockFile externalBufLockFileV2
 		if err := getUnmarshalStrict(allowJSON)(data, &externalBufLockFile); err != nil {
-			return nil, fmt.Errorf("invalid as version %v: %w", fileVersion, err)
+			return nil, err
 		}
 		depModuleKeys := make([]bufmodule.ModuleKey, len(externalBufLockFile.Deps))
 		for i, dep := range externalBufLockFile.Deps {
diff --git a/private/bufpkg/bufconfig/buf_work_yaml_file.go b/private/bufpkg/bufconfig/buf_work_yaml_file.go
index 91f03f4fad..dd85f1b566 100644
--- a/private/bufpkg/bufconfig/buf_work_yaml_file.go
+++ b/private/bufpkg/bufconfig/buf_work_yaml_file.go
@@ -186,7 +186,7 @@ func readBufWorkYAMLFile(
 	}
 	var externalBufWorkYAMLFile externalBufWorkYAMLFileV1
 	if err := getUnmarshalStrict(allowJSON)(data, &externalBufWorkYAMLFile); err != nil {
-		return nil, fmt.Errorf("invalid as version %v: %w", fileVersion, err)
+		return nil, err
 	}
 	return newBufWorkYAMLFile(fileVersion, objectData, externalBufWorkYAMLFile.Directories)
 }
diff --git a/private/bufpkg/bufconfig/buf_yaml_file.go b/private/bufpkg/bufconfig/buf_yaml_file.go
index 257dc105ce..73c2508da1 100644
--- a/private/bufpkg/bufconfig/buf_yaml_file.go
+++ b/private/bufpkg/bufconfig/buf_yaml_file.go
@@ -403,7 +403,7 @@ func readBufYAMLFile(
 	case FileVersionV1Beta1, FileVersionV1:
 		var externalBufYAMLFile externalBufYAMLFileV1Beta1V1
 		if err := getUnmarshalStrict(allowJSON)(data, &externalBufYAMLFile); err != nil {
-			return nil, fmt.Errorf("invalid as version %v: %w", fileVersion, err)
+			return nil, err
 		}
 		if fileVersion == FileVersionV1 && len(externalBufYAMLFile.Build.Roots) > 0 {
 			return nil, fmt.Errorf("build.roots cannot be set on version %v: %v", fileVersion, externalBufYAMLFile.Build.Roots)
@@ -475,7 +475,7 @@ func readBufYAMLFile(
 	case FileVersionV2:
 		var externalBufYAMLFile externalBufYAMLFileV2
 		if err := getUnmarshalStrict(allowJSON)(data, &externalBufYAMLFile); err != nil {
-			return nil, fmt.Errorf("invalid as version %v: %w", fileVersion, err)
+			return nil, err
 		}
 		externalModules := externalBufYAMLFile.Modules
 		if len(externalModules) == 0 {
diff --git a/private/bufpkg/bufpolicy/bufpolicyconfig/buf_policy_yaml_file.go b/private/bufpkg/bufpolicy/bufpolicyconfig/buf_policy_yaml_file.go
index 945f74b78a..7a6bf7e394 100644
--- a/private/bufpkg/bufpolicy/bufpolicyconfig/buf_policy_yaml_file.go
+++ b/private/bufpkg/bufpolicy/bufpolicyconfig/buf_policy_yaml_file.go
@@ -198,7 +198,7 @@ func readBufPolicyYAMLFile(
 	}
 	var externalBufPolicyYAMLFile externalBufPolicyYAMLFileV2
 	if err := getUnmarshalStrict(allowJSON)(data, &externalBufPolicyYAMLFile); err != nil {
-		return nil, fmt.Errorf("invalid as version %v: %w", fileVersion, err)
+		return nil, err
 	}
 	var lintConfig bufpolicy.LintConfig
 	if !externalBufPolicyYAMLFile.Lint.isEmpty() {
diff --git a/private/pkg/encoding/encoding.go b/private/pkg/encoding/encoding.go
index 16afbbcf58..73cc414b85 100644
--- a/private/pkg/encoding/encoding.go
+++ b/private/pkg/encoding/encoding.go
@@ -35,10 +35,7 @@ func UnmarshalJSONStrict(data []byte, v any) error {
 	}
 	jsonDecoder := json.NewDecoder(bytes.NewReader(data))
 	jsonDecoder.DisallowUnknownFields()
-	if err := jsonDecoder.Decode(v); err != nil {
-		return fmt.Errorf("could not unmarshal as JSON: %v", err)
-	}
-	return nil
+	return jsonDecoder.Decode(v)
 }
 
 // UnmarshalYAMLStrict unmarshals the data as YAML, returning a user error on failure.
@@ -49,10 +46,7 @@ func UnmarshalYAMLStrict(data []byte, v any) error {
 		return nil
 	}
 	yamlDecoder := NewYAMLDecoderStrict(bytes.NewReader(data))
-	if err := yamlDecoder.Decode(v); err != nil {
-		return fmt.Errorf("could not unmarshal as YAML: %v", err)
-	}
-	return nil
+	return updateYAMLTypeError(yamlDecoder.Decode(v))
 }
 
 // UnmarshalJSONOrYAMLStrict unmarshals the data as JSON or YAML in order, returning
@@ -79,10 +73,7 @@ func UnmarshalJSONNonStrict(data []byte, v any) error {
 		return nil
 	}
 	jsonDecoder := json.NewDecoder(bytes.NewReader(data))
-	if err := jsonDecoder.Decode(v); err != nil {
-		return fmt.Errorf("could not unmarshal as JSON: %v", err)
-	}
-	return nil
+	return jsonDecoder.Decode(v)
 }
 
 // UnmarshalYAMLNonStrict unmarshals the data as YAML, returning a user error on failure.
@@ -93,10 +84,7 @@ func UnmarshalYAMLNonStrict(data []byte, v any) error {
 		return nil
 	}
 	yamlDecoder := NewYAMLDecoderNonStrict(bytes.NewReader(data))
-	if err := yamlDecoder.Decode(v); err != nil {
-		return fmt.Errorf("could not unmarshal as YAML: %v", err)
-	}
-	return nil
+	return updateYAMLTypeError(yamlDecoder.Decode(v))
 }
 
 // UnmarshalJSONOrYAMLNonStrict unmarshals the data as JSON or YAML in order, returning
@@ -200,3 +188,34 @@ func InterfaceSliceOrStringToStringSlice(in any) ([]string, error) {
 		return nil, fmt.Errorf("could not interpret %T as string or string slice", in)
 	}
 }
+
+// *** PRIVATE ***
+
+func updateYAMLTypeError(err error) error {
+	if err == nil {
+		return nil
+	}
+	var yamlTypeError *yaml.TypeError
+	if errors.As(err, &yamlTypeError) {
+		for i, errString := range yamlTypeError.Errors {
+			yamlTypeError.Errors[i] = replaceAfter(
+				replaceAfter(
+					errString,
+					"already set in type",
+					"already set",
+				),
+				"not found in type",
+				"not found",
+			)
+		}
+		return yamlTypeError
+	}
+	return err
+}
+
+func replaceAfter(s string, substitute string, replace string) string {
+	if index := strings.Index(s, substitute); index != -1 {
+		return s[:index] + replace
+	}
+	return s
+}