diff --git a/pkg/errors/error.go b/pkg/errors/error.go
index be2cf58f9..01789b708 100644
--- a/pkg/errors/error.go
+++ b/pkg/errors/error.go
@@ -3,6 +3,7 @@ package errors
 import (
 	"context"
 	"fmt"
+	"net/http"
 
 	"github.com/github/github-mcp-server/pkg/utils"
 	"github.com/google/go-github/v79/github"
@@ -44,10 +45,25 @@ func (e *GitHubGraphQLError) Error() string {
 	return fmt.Errorf("%s: %w", e.Message, e.Err).Error()
 }
 
+type GitHubRawAPIError struct {
+	Message  string         `json:"message"`
+	Response *http.Response `json:"-"`
+	Err      error          `json:"-"`
+}
+
+func newGitHubRawAPIError(message string, resp *http.Response, err error) *GitHubRawAPIError {
+	return &GitHubRawAPIError{
+		Message:  message,
+		Response: resp,
+		Err:      err,
+	}
+}
+
 type GitHubErrorKey struct{}
 type GitHubCtxErrors struct {
 	api     []*GitHubAPIError
 	graphQL []*GitHubGraphQLError
+	raw     []*GitHubRawAPIError
 }
 
 // ContextWithGitHubErrors updates or creates a context with a pointer to GitHub error information (to be used by middleware).
@@ -59,6 +75,7 @@ func ContextWithGitHubErrors(ctx context.Context) context.Context {
 		// If the context already has GitHubCtxErrors, we just empty the slices to start fresh
 		val.api = []*GitHubAPIError{}
 		val.graphQL = []*GitHubGraphQLError{}
+		val.raw = []*GitHubRawAPIError{}
 	} else {
 		// If not, we create a new GitHubCtxErrors and set it in the context
 		ctx = context.WithValue(ctx, GitHubErrorKey{}, &GitHubCtxErrors{})
@@ -83,6 +100,14 @@ func GetGitHubGraphQLErrors(ctx context.Context) ([]*GitHubGraphQLError, error)
 	return nil, fmt.Errorf("context does not contain GitHubCtxErrors")
 }
 
+// GetGitHubRawAPIErrors retrieves the slice of GitHubRawAPIErrors from the context.
+func GetGitHubRawAPIErrors(ctx context.Context) ([]*GitHubRawAPIError, error) {
+	if val, ok := ctx.Value(GitHubErrorKey{}).(*GitHubCtxErrors); ok {
+		return val.raw, nil // return the slice of raw API errors from the context
+	}
+	return nil, fmt.Errorf("context does not contain GitHubCtxErrors")
+}
+
 func NewGitHubAPIErrorToCtx(ctx context.Context, message string, resp *github.Response, err error) (context.Context, error) {
 	apiErr := newGitHubAPIError(message, resp, err)
 	if ctx != nil {
@@ -107,6 +132,15 @@ func addGitHubGraphQLErrorToContext(ctx context.Context, err *GitHubGraphQLError
 	return nil, fmt.Errorf("context does not contain GitHubCtxErrors")
 }
 
+func addRawAPIErrorToContext(ctx context.Context, err *GitHubRawAPIError) (context.Context, error) {
+	if val, ok := ctx.Value(GitHubErrorKey{}).(*GitHubCtxErrors); ok {
+		val.raw = append(val.raw, err)
+		return ctx, nil
+	}
+
+	return nil, fmt.Errorf("context does not contain GitHubCtxErrors")
+}
+
 // NewGitHubAPIErrorResponse returns an mcp.NewToolResultError and retains the error in the context for access via middleware
 func NewGitHubAPIErrorResponse(ctx context.Context, message string, resp *github.Response, err error) *mcp.CallToolResult {
 	apiErr := newGitHubAPIError(message, resp, err)
@@ -124,3 +158,11 @@ func NewGitHubGraphQLErrorResponse(ctx context.Context, message string, err erro
 	}
 	return utils.NewToolResultErrorFromErr(message, err)
 }
+
+func NewGitHubRawAPIErrorResponse(ctx context.Context, message string, resp *http.Response, err error) *mcp.CallToolResult {
+	rawAPIErr := newGitHubRawAPIError(message, resp, err)
+	if ctx != nil {
+		_, _ = addRawAPIErrorToContext(ctx, rawAPIErr) // Explicitly ignore error for graceful handling
+	}
+	return utils.NewToolResultErrorFromErr(message, err)
+}
diff --git a/pkg/github/repositories.go b/pkg/github/repositories.go
index e5f6ec0c1..5066e9642 100644
--- a/pkg/github/repositories.go
+++ b/pkg/github/repositories.go
@@ -636,7 +636,7 @@ func GetFileContents(getClient GetClientFn, getRawClient raw.GetRawClientFn, t t
 			}
 			resp, err := rawClient.GetRawContent(ctx, owner, repo, path, rawOpts)
 			if err != nil {
-				return utils.NewToolResultError("failed to get raw repository content"), nil, nil
+				return ghErrors.NewGitHubRawAPIErrorResponse(ctx, "failed to get raw repository content", resp, err), nil, nil
 			}
 			defer func() {
 				_ = resp.Body.Close()