diff --git a/diff/diff_error_test.go b/diff/diff_error_test.go
index 08c375a5..babb8baa 100644
--- a/diff/diff_error_test.go
+++ b/diff/diff_error_test.go
@@ -240,5 +240,5 @@ func TestDiff_ComponentCallbacksNil(t *testing.T) {
 
 func TestFilterByRegex_Invalid(t *testing.T) {
 	_, err := diff.Get(&diff.Config{PathFilter: "["}, l(t, 1), l(t, 2))
-	require.EqualError(t, err, "failed to compile filter regex \"[\" with error parsing regexp: missing closing ]: `[`")
+	require.EqualError(t, err, "failed to compile filter regex \"[\": error parsing regexp: missing closing ]: `[`")
 }
diff --git a/diff/example_test.go b/diff/example_test.go
index b04eae8c..58f8d496 100644
--- a/diff/example_test.go
+++ b/diff/example_test.go
@@ -18,13 +18,13 @@ func ExampleGet() {
 
 	s1, err := loader.LoadFromFile("../data/simple1.yaml")
 	if err != nil {
-		fmt.Fprintf(os.Stderr, "failed to load spec with %v", err)
+		fmt.Fprintf(os.Stderr, "failed to load spec: %v", err)
 		return
 	}
 
 	s2, err := loader.LoadFromFile("../data/simple2.yaml")
 	if err != nil {
-		fmt.Fprintf(os.Stderr, "failed to load spec with %v", err)
+		fmt.Fprintf(os.Stderr, "failed to load spec: %v", err)
 		return
 	}
 
@@ -66,13 +66,13 @@ func ExampleGetPathsDiff() {
 
 	s1, err := load.NewSpecInfo(loader, load.NewSource("../data/openapi-test1.yaml"))
 	if err != nil {
-		fmt.Fprintf(os.Stderr, "failed to load spec with %v", err)
+		fmt.Fprintf(os.Stderr, "failed to load spec: %v", err)
 		return
 	}
 
 	s2, err := load.NewSpecInfo(loader, load.NewSource("../data/openapi-test3.yaml"))
 	if err != nil {
-		fmt.Fprintf(os.Stderr, "failed to load spec with %v", err)
+		fmt.Fprintf(os.Stderr, "failed to load spec: %v", err)
 		return
 	}
 
diff --git a/diff/operations_diff.go b/diff/operations_diff.go
index d0f4ba9e..e053c89c 100644
--- a/diff/operations_diff.go
+++ b/diff/operations_diff.go
@@ -130,7 +130,7 @@ func filterOperationsByExtensions(filterExtension string, pathItemPair *pathItem
 
 	r, err := regexp.Compile(filterExtension)
 	if err != nil {
-		return fmt.Errorf("failed to compile extension filter regex %q with %w", filterExtension, err)
+		return fmt.Errorf("failed to compile extension filter regex %q: %w", filterExtension, err)
 	}
 
 	filterOperationsByExtensionInternal(pathItemPair.PathItem1, r)
diff --git a/diff/paths_diff.go b/diff/paths_diff.go
index b038a517..8678dc45 100644
--- a/diff/paths_diff.go
+++ b/diff/paths_diff.go
@@ -123,7 +123,7 @@ func filterPathsByName(filter string, paths1, paths2 *openapi3.Paths) error {
 
 	r, err := regexp.Compile(filter)
 	if err != nil {
-		return fmt.Errorf("failed to compile filter regex %q with %w", filter, err)
+		return fmt.Errorf("failed to compile filter regex %q: %w", filter, err)
 	}
 
 	filterPathsInternal(paths1, r)
@@ -147,7 +147,7 @@ func filterPathsByExtensions(filterExtension string, paths1, paths2 *openapi3.Pa
 
 	r, err := regexp.Compile(filterExtension)
 	if err != nil {
-		return fmt.Errorf("failed to compile extension filter regex %q with %w", filterExtension, err)
+		return fmt.Errorf("failed to compile extension filter regex %q: %w", filterExtension, err)
 	}
 
 	filterPathsByExtensionInternal(paths1, r)
diff --git a/flatten/allof/merge_allof_spec_test.go b/flatten/allof/merge_allof_spec_test.go
index 4b0bd787..48fff4f7 100644
--- a/flatten/allof/merge_allof_spec_test.go
+++ b/flatten/allof/merge_allof_spec_test.go
@@ -24,5 +24,5 @@ func Test_MergeSpecOK(t *testing.T) {
 
 func Test_MergeSpecInvalid(t *testing.T) {
 	_, err := load.NewSpecInfo(openapi3.NewLoader(), load.NewSource("../../data/allof/invalid.yaml"), load.WithFlattenAllOf())
-	require.EqualError(t, err, "unable to resolve Type conflict: all Type values must be identical")
+	require.EqualError(t, err, "failed to flatten allOf in \"../../data/allof/invalid.yaml\": unable to resolve Type conflict: all Type values must be identical")
 }
diff --git a/internal/errors.go b/internal/errors.go
index 322aea01..190c4cbe 100644
--- a/internal/errors.go
+++ b/internal/errors.go
@@ -22,28 +22,28 @@ func getErrInvalidFlags(err error) *ReturnError {
 
 func getErrFailedToLoadSpec(what string, source *load.Source, err error) *ReturnError {
 	return getError(
-		fmt.Errorf("failed to load %s spec from %s with %v", what, source.Out(), err),
+		fmt.Errorf("failed to load %s spec from %s: %w", what, source.Out(), err),
 		102,
 	)
 }
 
 func getErrFailedToLoadSpecs(what string, path string, err error) *ReturnError {
 	return getError(
-		fmt.Errorf("failed to load %s specs from glob %q with %v", what, path, err),
+		fmt.Errorf("failed to load %s specs from glob %q: %w", what, path, err),
 		103,
 	)
 }
 
 func getErrDiffFailed(err error) *ReturnError {
 	return getError(
-		fmt.Errorf("diff failed with %v", err),
+		fmt.Errorf("diff failed: %w", err),
 		104,
 	)
 }
 
 func getErrFailedPrint(what string, err error) *ReturnError {
 	return getError(
-		fmt.Errorf("failed to print %q with %v", what, err),
+		fmt.Errorf("failed to print %q: %w", what, err),
 		105,
 	)
 }
@@ -92,7 +92,7 @@ func getErrInvalidColorMode(err error) *ReturnError {
 
 func getErrCantProcessIgnoreFile(what string, err error) *ReturnError {
 	return getError(
-		fmt.Errorf("can't process %s ignore file %v", what, err),
+		fmt.Errorf("can't process %s ignore file: %w", what, err),
 		121,
 	)
 }
diff --git a/internal/run_test.go b/internal/run_test.go
index f1f7d826..144afe90 100644
--- a/internal/run_test.go
+++ b/internal/run_test.go
@@ -78,27 +78,27 @@ func Test_InvalidFile(t *testing.T) {
 	var stderr bytes.Buffer
 	require.Equal(t, 102, internal.Run(cmdToArgs("oasdiff diff no-file ../data/openapi-test3.yaml"), io.Discard, &stderr))
 	require.Condition(t, func() (success bool) {
-		return stderr.String() == "Error: failed to load base spec from \"no-file\" with open no-file: no such file or directory\n" ||
-			stderr.String() == "Error: failed to load base spec from \"no-file\" with open no-file: The system cannot find the file specified.\n" // windows
-	})
+		return stderr.String() == "Error: failed to load base spec from \"no-file\": open no-file: no such file or directory\n" ||
+			stderr.String() == "Error: failed to load base spec from \"no-file\": open no-file: The system cannot find the file specified.\n" // windows
+	}, stderr.String())
 }
 
 func Test_InvalidGlob(t *testing.T) {
 	var stderr bytes.Buffer
 	require.Equal(t, 103, internal.Run(cmdToArgs(`oasdiff diff -c "a[" ../data/openapi-test3.yaml`), io.Discard, &stderr))
-	require.Equal(t, "Error: failed to load base specs from glob \"\\\"a[\\\"\" with syntax error in pattern\n", stderr.String())
+	require.Equal(t, "Error: failed to load base specs from glob \"\\\"a[\\\"\": syntax error in pattern\n", stderr.String())
 }
 
 func Test_GlobNoFiles(t *testing.T) {
 	var stderr bytes.Buffer
 	require.Equal(t, 103, internal.Run(cmdToArgs("oasdiff diff -c no-file ../data/openapi-test3.yaml"), io.Discard, &stderr))
-	require.Equal(t, "Error: failed to load base specs from glob \"no-file\" with no matching files\n", stderr.String())
+	require.Equal(t, "Error: failed to load base specs from glob \"no-file\": no matching files\n", stderr.String())
 }
 
 func Test_GlobWithUrl(t *testing.T) {
 	var stderr bytes.Buffer
 	require.Equal(t, 103, internal.Run(cmdToArgs("oasdiff diff -c ../data/openapi-test1.yaml https://"), io.Discard, &stderr))
-	require.Equal(t, "Error: failed to load revision specs from glob \"https://\" with no matching files (should be a glob, not a URL)\n", stderr.String())
+	require.Equal(t, "Error: failed to load revision specs from glob \"https://\": no matching files (should be a glob, not a URL)\n", stderr.String())
 }
 
 func Test_DiffInvalidFormat(t *testing.T) {
@@ -202,6 +202,13 @@ func Test_ComposedMode(t *testing.T) {
 	require.Equal(t, map[string]interface{}{"paths": map[string]interface{}{"deleted": []interface{}{"/api/old-test"}}}, bc)
 }
 
+func Test_ComposedModeInvalidFile(t *testing.T) {
+	var stderr bytes.Buffer
+	require.Equal(t, 103, internal.Run(cmdToArgs("oasdiff diff ../data/allof/* ../data/allof/* --composed --flatten"), io.Discard, &stderr))
+	require.Equal(t, `Error: failed to load base specs from glob "../data/allof/*": failed to flatten allOf in "../data/allof/invalid.yaml": unable to resolve Type conflict: all Type values must be identical
+`, stderr.String())
+}
+
 func Test_Help(t *testing.T) {
 	var stdout bytes.Buffer
 	require.Zero(t, internal.Run(cmdToArgs("oasdiff --help"), &stdout, io.Discard))
@@ -285,7 +292,7 @@ func Test_FlattenCmdOK(t *testing.T) {
 func Test_FlattenCmdInvalid(t *testing.T) {
 	var stderr bytes.Buffer
 	require.Equal(t, 102, internal.Run(cmdToArgs("oasdiff flatten ../data/allof/invalid.yaml"), io.Discard, &stderr))
-	require.Equal(t, `Error: failed to load original spec from "../data/allof/invalid.yaml" with unable to resolve Type conflict: all Type values must be identical
+	require.Equal(t, `Error: failed to load original spec from "../data/allof/invalid.yaml": failed to flatten allOf in "../data/allof/invalid.yaml": unable to resolve Type conflict: all Type values must be identical
 `, stderr.String())
 }
 
diff --git a/load/option.go b/load/option.go
index bc408ae3..bcaaa1b4 100644
--- a/load/option.go
+++ b/load/option.go
@@ -1,6 +1,8 @@
 package load
 
 import (
+	"fmt"
+
 	"github.com/tufin/oasdiff/flatten/allof"
 	"github.com/tufin/oasdiff/flatten/commonparams"
 	"github.com/tufin/oasdiff/flatten/headers"
@@ -30,7 +32,7 @@ func WithFlattenAllOf() Option {
 		var err error
 		for _, specInfo := range specInfos {
 			if specInfo.Spec, err = allof.MergeSpec(specInfo.Spec); err != nil {
-				return nil, err
+				return nil, fmt.Errorf("failed to flatten allOf in %q: %w", specInfo.Url, err)
 			}
 		}
 		return specInfos, nil
diff --git a/load/spec_info.go b/load/spec_info.go
index f1f57b58..01710fe4 100644
--- a/load/spec_info.go
+++ b/load/spec_info.go
@@ -2,6 +2,7 @@ package load
 
 import (
 	"errors"
+	"fmt"
 	"net/url"
 
 	"github.com/getkin/kin-openapi/openapi3"
@@ -86,7 +87,7 @@ func fromGlob(loader Loader, glob string) ([]*SpecInfo, error) {
 	for _, file := range files {
 		spec, err := loader.LoadFromFile(file)
 		if err != nil {
-			return nil, err
+			return nil, fmt.Errorf("failed to load %q: %w", file, err)
 		}
 		result = append(result, &SpecInfo{Url: file, Spec: spec})
 	}
diff --git a/load/spec_info_test.go b/load/spec_info_test.go
index de7e90c0..77c77627 100644
--- a/load/spec_info_test.go
+++ b/load/spec_info_test.go
@@ -111,7 +111,7 @@ func TestSpecInfo_GlobOK(t *testing.T) {
 
 func TestSpecInfo_InvalidSpec(t *testing.T) {
 	_, err := load.NewSpecInfoFromGlob(MockLoader{}, "../data/ignore-err-example.txt")
-	require.EqualError(t, err, "error unmarshaling JSON: while decoding JSON: json: cannot unmarshal string into Go value of type openapi3.TBis")
+	require.EqualError(t, err, "failed to load \"../data/ignore-err-example.txt\": error unmarshaling JSON: while decoding JSON: json: cannot unmarshal string into Go value of type openapi3.TBis")
 }
 
 func TestSpecInfo_InvalidGlob(t *testing.T) {