diff --git a/internal/fingerprint/fingerprint.go b/internal/fingerprint/fingerprint.go
index 67f889bd..d5e62a63 100644
--- a/internal/fingerprint/fingerprint.go
+++ b/internal/fingerprint/fingerprint.go
@@ -1,9 +1,11 @@
 package fingerprint
 
 import (
+	"archive/zip"
 	"bufio"
 	"crypto/md5" // #nosec
 	"fmt"
+	"io"
 	"log"
 	"os"
 	"path/filepath"
@@ -109,6 +111,7 @@ func (f FileFingerprint) ToString() string {
 
 	return fmt.Sprintf("file=%x,%d,%s", f.fingerprint, f.contentLength, path)
 }
+
 func (f *Fingerprinter) FingerprintFiles(rootPath string, exclusions []string) (Fingerprints, error) {
 	log.Println("Warning: Fingerprinting is beta and may not work as expected.")
 	if len(rootPath) == 0 {
@@ -132,12 +135,21 @@ func (f *Fingerprinter) FingerprintFiles(rootPath string, exclusions []string) (
 			return nil
 		}
 
+		// Scan the contents of compressed files
+		// such as .jar and .nupkg
+		if shouldUnzip(path) {
+			fingerprintsZip, err := inMemFingerprintingCompressedContent(path, exclusions)
+			if err != nil {
+				return err
+			}
+			fingerprints.Entries = append(fingerprints.Entries, fingerprintsZip...)
+			nbFiles += len(fingerprintsZip)
+		}
 		nbFiles++
 		fingerprint, err := computeMD5(path)
 		if err != nil {
 			return err
 		}
-
 		fingerprints.Append(fingerprint)
 
 		if nbFiles%100 == 0 {
@@ -184,6 +196,12 @@ func shouldProcessFile(fileInfo os.FileInfo, exclusions []string, path string) b
 
 	isSymlink, err := isSymlink(path)
 	if err != nil {
+		// If we get a "not a directory" error, we can assume it's not a symlink
+		// otherwise, we don't know, so we return false
+		return strings.HasSuffix(err.Error(), "not a directory")
+	}
+
+	if isSymlink {
 		return false
 	}
 
@@ -246,3 +264,53 @@ func (f *Fingerprints) ToFile(ouputFile string) error {
 func (f *Fingerprints) Append(fingerprint FileFingerprint) {
 	f.Entries = append(f.Entries, fingerprint)
 }
+
+var filesToUnzip = []string{".jar", ".nupkg"}
+
+func shouldUnzip(filename string) bool {
+	for _, file := range filesToUnzip {
+		if filepath.Ext(filename) == file {
+			return true
+		}
+	}
+
+	return false
+}
+
+func inMemFingerprintingCompressedContent(filename string, exclusions []string) ([]FileFingerprint, error) {
+
+	r, err := zip.OpenReader(filename)
+	if err != nil {
+		return nil, err
+	}
+	defer r.Close()
+
+	fingerprints := []FileFingerprint{}
+
+	for _, f := range r.File {
+		longFileNmae := fmt.Sprintf("%s/%s", filename, f.Name)
+
+		if !shouldProcessFile(f.FileInfo(), exclusions, longFileNmae) {
+			continue
+		}
+		rc, err := f.Open()
+		if err != nil {
+			return nil, err
+		}
+		hasher := md5.New()
+		_, err = io.Copy(hasher, rc)
+		if err != nil {
+			return nil, err
+		}
+
+		fingerprints = append(fingerprints, FileFingerprint{
+			path:          longFileNmae,
+			contentLength: int64(f.UncompressedSize64),
+			fingerprint:   hasher.Sum(nil),
+		})
+
+		rc.Close()
+	}
+
+	return fingerprints, nil
+}
diff --git a/internal/fingerprint/fingerprint_test.go b/internal/fingerprint/fingerprint_test.go
index 8319de9c..a39c7e99 100644
--- a/internal/fingerprint/fingerprint_test.go
+++ b/internal/fingerprint/fingerprint_test.go
@@ -4,6 +4,7 @@ import (
 	"fmt"
 	"os"
 	"path/filepath"
+	"strings"
 	"testing"
 
 	"github.com/stretchr/testify/assert"
@@ -162,3 +163,80 @@ func TestFingerprintsToFile(t *testing.T) {
 	assert.NoError(t, err)
 
 }
+
+func TestShouldUnzip(t *testing.T) {
+	tests := []struct {
+		name     string
+		filename string
+		want     bool
+	}{
+		{
+			name:     "Should unzip .jar file",
+			filename: "test.jar",
+			want:     true,
+		},
+		{
+			name:     "Should unzip .nupkg file",
+			filename: "test.nupkg",
+			want:     true,
+		},
+		{
+			name:     "Should not unzip .txt file",
+			filename: "test.txt",
+			want:     false,
+		},
+		{
+			name:     "Should not unzip .go file",
+			filename: "test.go",
+			want:     false,
+		},
+		{
+			name:     "Should pick up .jar file in nested folder",
+			filename: "deep/folder/test.jar",
+			want:     true,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			if got := shouldUnzip(tt.filename); got != tt.want {
+				t.Errorf("shouldUnzip() = %v, want %v", got, tt.want)
+			}
+		})
+	}
+}
+
+func TestInMemFingerprintingCompressedContent(t *testing.T) {
+	tests := []struct {
+		name     string
+		path     string
+		expected int
+		suffix   string
+	}{
+		{
+			name:     "Jar",
+			path:     "testdata/zipfile/jar",
+			expected: 5,
+			suffix:   "log4j:log4j-api-2.18.0.jar",
+		},
+		{
+			name:     "Nupkg",
+			path:     "testdata/zipfile/nupkg",
+			expected: 22,
+			suffix:   "newtonsoft.json.13.0.3.nupkg",
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			fingerprinter := NewFingerprinter()
+			fingerprints, err := fingerprinter.FingerprintFiles(tt.path, []string{})
+			assert.NoError(t, err)
+			assert.NotNil(t, fingerprints)
+			assert.NotEmpty(t, fingerprints)
+			assert.Equal(t, tt.expected, fingerprints.Len())
+			lastRow := fingerprints.Entries[len(fingerprints.Entries)-1]
+			assert.True(t, strings.HasSuffix(lastRow.ToString(), tt.suffix))
+		})
+	}
+}
diff --git a/internal/fingerprint/testdata/zipfile/jar/log4j:log4j-api-2.18.0.jar b/internal/fingerprint/testdata/zipfile/jar/log4j:log4j-api-2.18.0.jar
new file mode 100644
index 00000000..b4e933f7
Binary files /dev/null and b/internal/fingerprint/testdata/zipfile/jar/log4j:log4j-api-2.18.0.jar differ
diff --git a/internal/fingerprint/testdata/zipfile/nupkg/newtonsoft.json.13.0.3.nupkg b/internal/fingerprint/testdata/zipfile/nupkg/newtonsoft.json.13.0.3.nupkg
new file mode 100644
index 00000000..5829e3da
Binary files /dev/null and b/internal/fingerprint/testdata/zipfile/nupkg/newtonsoft.json.13.0.3.nupkg differ