diff --git a/pkg/handlers/archive.go b/pkg/handlers/archive.go
index 151b72830307..f743c2c9f942 100644
--- a/pkg/handlers/archive.go
+++ b/pkg/handlers/archive.go
@@ -246,8 +246,9 @@ func ensureToolsForMimeType(mimeType string) error {
 // and processes it based on its extension, such as handling Debian (.deb) and RPM (.rpm) packages.
 // It returns an io.Reader that can be used to read the processed content of the file,
 // and an error if any issues occurred during processing.
+// If the file is specialized, the returned boolean is true with no error.
 // The caller is responsible for closing the returned reader.
-func (a *Archive) HandleSpecialized(ctx context.Context, reader io.Reader) (io.Reader, bool, error) {
+func (a *Archive) HandleSpecialized(ctx logContext.Context, reader io.Reader) (io.Reader, bool, error) {
 	mimeType, reader, err := determineMimeType(reader)
 	if err != nil {
 		return nil, false, err
@@ -279,7 +280,7 @@ func (a *Archive) HandleSpecialized(ctx context.Context, reader io.Reader) (io.R
 // It handles the extraction process by using the 'ar' command and manages temporary
 // files and directories for the operation.
 // The caller is responsible for closing the returned reader.
-func (a *Archive) extractDebContent(ctx context.Context, file io.Reader) (io.ReadCloser, error) {
+func (a *Archive) extractDebContent(ctx logContext.Context, file io.Reader) (io.ReadCloser, error) {
 	if a.currentDepth >= maxDepth {
 		return nil, fmt.Errorf("max archive depth reached")
 	}
@@ -297,7 +298,7 @@ func (a *Archive) extractDebContent(ctx context.Context, file io.Reader) (io.Rea
 		return nil, err
 	}
 
-	handler := func(ctx context.Context, env tempEnv, file string) (string, error) {
+	handler := func(ctx logContext.Context, env tempEnv, file string) (string, error) {
 		if strings.HasPrefix(file, "data.tar.") {
 			return file, nil
 		}
@@ -317,7 +318,7 @@ func (a *Archive) extractDebContent(ctx context.Context, file io.Reader) (io.Rea
 // It handles the extraction process by using the 'rpm2cpio' and 'cpio' commands and manages temporary
 // files and directories for the operation.
 // The caller is responsible for closing the returned reader.
-func (a *Archive) extractRpmContent(ctx context.Context, file io.Reader) (io.ReadCloser, error) {
+func (a *Archive) extractRpmContent(ctx logContext.Context, file io.Reader) (io.ReadCloser, error) {
 	if a.currentDepth >= maxDepth {
 		return nil, fmt.Errorf("max archive depth reached")
 	}
@@ -336,7 +337,7 @@ func (a *Archive) extractRpmContent(ctx context.Context, file io.Reader) (io.Rea
 		return nil, err
 	}
 
-	handler := func(ctx context.Context, env tempEnv, file string) (string, error) {
+	handler := func(ctx logContext.Context, env tempEnv, file string) (string, error) {
 		if strings.HasSuffix(file, ".tar.gz") {
 			return file, nil
 		}
@@ -351,7 +352,7 @@ func (a *Archive) extractRpmContent(ctx context.Context, file io.Reader) (io.Rea
 	return openDataArchive(tmpEnv.extractPath, dataArchiveName)
 }
 
-func (a *Archive) handleNestedFileMIME(ctx context.Context, tempEnv tempEnv, fileName string) (string, error) {
+func (a *Archive) handleNestedFileMIME(ctx logContext.Context, tempEnv tempEnv, fileName string) (string, error) {
 	nestedFile, err := os.Open(filepath.Join(tempEnv.extractPath, fileName))
 	if err != nil {
 		return "", err
@@ -360,7 +361,7 @@ func (a *Archive) handleNestedFileMIME(ctx context.Context, tempEnv tempEnv, fil
 
 	mimeType, reader, err := determineMimeType(nestedFile)
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("unable to determine MIME type of nested filename: %s, %w", nestedFile.Name(), err)
 	}
 
 	switch mimeType {
@@ -373,7 +374,7 @@ func (a *Archive) handleNestedFileMIME(ctx context.Context, tempEnv tempEnv, fil
 	}
 
 	if err != nil {
-		return "", err
+		return "", fmt.Errorf("unable to extract file with MIME type %s: %w", mimeType, err)
 	}
 
 	return fileName, nil
@@ -405,7 +406,7 @@ func determineMimeType(reader io.Reader) (string, io.Reader, error) {
 // of the data archive it finds. This centralizes the logic for handling specialized files such as .deb and .rpm
 // by using the appropriate handling function passed as an argument. This design allows for flexibility and reuse
 // of this function across various extraction processes in the package.
-func (a *Archive) handleExtractedFiles(ctx context.Context, env tempEnv, handleFile func(context.Context, tempEnv, string) (string, error)) (string, error) {
+func (a *Archive) handleExtractedFiles(ctx logContext.Context, env tempEnv, handleFile func(logContext.Context, tempEnv, string) (string, error)) (string, error) {
 	extractedFiles, err := os.ReadDir(env.extractPath)
 	if err != nil {
 		return "", fmt.Errorf("unable to read extracted directory: %w", err)
@@ -462,7 +463,7 @@ func executeCommand(cmd *exec.Cmd) error {
 	var stderr bytes.Buffer
 	cmd.Stderr = &stderr
 	if err := cmd.Run(); err != nil {
-		return fmt.Errorf("unable to execute command: %w; error: %s", err, stderr.String())
+		return fmt.Errorf("unable to execute command %v: %w; error: %s", cmd.String(), err, stderr.String())
 	}
 	return nil
 }
diff --git a/pkg/handlers/archive_test.go b/pkg/handlers/archive_test.go
index 9608ad43e9c8..9b43582983e6 100644
--- a/pkg/handlers/archive_test.go
+++ b/pkg/handlers/archive_test.go
@@ -12,6 +12,7 @@ import (
 	diskbufferreader "github.com/bill-rich/disk-buffer-reader"
 	"github.com/stretchr/testify/assert"
 
+	logContext "github.com/trufflesecurity/trufflehog/v3/pkg/context"
 	"github.com/trufflesecurity/trufflehog/v3/pkg/sources"
 )
 
@@ -131,7 +132,7 @@ func TestExtractDebContent(t *testing.T) {
 	assert.Nil(t, err)
 	defer file.Close()
 
-	ctx := context.Background()
+	ctx := logContext.AddLogger(context.Background())
 	a := &Archive{}
 
 	reader, err := a.extractDebContent(ctx, file)
@@ -149,7 +150,7 @@ func TestExtractRPMContent(t *testing.T) {
 	assert.Nil(t, err)
 	defer file.Close()
 
-	ctx := context.Background()
+	ctx := logContext.AddLogger(context.Background())
 	a := &Archive{}
 
 	reader, err := a.extractRpmContent(ctx, file)
diff --git a/pkg/handlers/handlers.go b/pkg/handlers/handlers.go
index 31696483e2bf..cb18f7dd8eb9 100644
--- a/pkg/handlers/handlers.go
+++ b/pkg/handlers/handlers.go
@@ -4,6 +4,9 @@ import (
 	"context"
 	"io"
 
+	diskbufferreader "github.com/bill-rich/disk-buffer-reader"
+
+	logContext "github.com/trufflesecurity/trufflehog/v3/pkg/context"
 	"github.com/trufflesecurity/trufflehog/v3/pkg/sources"
 )
 
@@ -19,7 +22,7 @@ type SpecializedHandler interface {
 	// HandleSpecialized examines the provided file reader within the context and determines if it is a specialized archive.
 	// It returns a reader with any necessary modifications, a boolean indicating if the file was specialized,
 	// and an error if something went wrong during processing.
-	HandleSpecialized(context.Context, io.Reader) (io.Reader, bool, error)
+	HandleSpecialized(logContext.Context, io.Reader) (io.Reader, bool, error)
 }
 
 type Handler interface {
@@ -35,23 +38,40 @@ type Handler interface {
 // The function returns true if processing was successful and false otherwise.
 // Context is used for cancellation, and the caller is responsible for canceling it if needed.
 func HandleFile(ctx context.Context, file io.Reader, chunkSkel *sources.Chunk, chunksChan chan *sources.Chunk) bool {
+	aCtx := logContext.AddLogger(ctx)
 	for _, h := range DefaultHandlers() {
 		h.New()
-		var (
-			isSpecial bool
-			err       error
-		)
+
+		// The re-reader is used to reset the file reader after checking if the handler implements SpecializedHandler.
+		// This is necessary because the archive pkg doesn't correctly determine the file type when using
+		// an io.MultiReader, which is used by the SpecializedHandler.
+		reReader, err := diskbufferreader.New(file)
+		if err != nil {
+			aCtx.Logger().Error(err, "error creating re-reader reader")
+			return false
+		}
+		defer reReader.Close()
 
 		// Check if the handler implements SpecializedHandler and process accordingly.
 		if specialHandler, ok := h.(SpecializedHandler); ok {
-			if file, isSpecial, err = specialHandler.HandleSpecialized(ctx, file); isSpecial && err == nil {
-				return handleChunks(ctx, h.FromFile(ctx, file), chunkSkel, chunksChan)
+			file, isSpecial, err := specialHandler.HandleSpecialized(aCtx, reReader)
+			if isSpecial {
+				return handleChunks(aCtx, h.FromFile(ctx, file), chunkSkel, chunksChan)
+			}
+
+			if err != nil {
+				aCtx.Logger().Error(err, "error handling file")
 			}
 		}
 
+		if err := reReader.Reset(); err != nil {
+			aCtx.Logger().Error(err, "error resetting re-reader")
+			return false
+		}
+		reReader.Stop()
 		var isType bool
-		if file, isType = h.IsFiletype(ctx, file); isType {
-			return handleChunks(ctx, h.FromFile(ctx, file), chunkSkel, chunksChan)
+		if file, isType = h.IsFiletype(aCtx, reReader); isType {
+			return handleChunks(aCtx, h.FromFile(ctx, file), chunkSkel, chunksChan)
 		}
 	}
 	return false