Course contents

Unit 6: Advanced securityLesson 6.9 (5 of 11 in this unit)7 of 25 in the Advanced Cisco SD-WAN course

HTTPS/TLS proxy

How an edge decrypts and re-encrypts web traffic so other features can inspect it: certificates, what to decrypt and what to skip, and the limits.

Advanced · 13 min read

You'll learn to explain how the TLS proxy on a WAN Edge works, decide what to decrypt and what to bypass, and predict which traffic it cannot inspect.

Technical definition

TLS proxy (also called an SSL proxy) is a function on the WAN Edge that ends the client's TLS session, opens a second TLS session to the real server, and inspects the clear text between the two. It then re-encrypts the data before passing it on. The client sees a certificate issued by the organisation's own certificate authority (CA) instead of the server's.

Why inspection features go blind without it

Most web traffic is HTTPS, which is HTTP carried inside TLS (Transport Layer Security, the encryption protocol that replaced SSL). An IPS looks for attack patterns in the data. A malware scanner looks at files. A URL filter wants the path of a page. When the data is encrypted, all three see very little. The TLS proxy on the WAN Edge (cEdge/vEdge) exists to give those features something to read.

It does this as a deliberate man in the middle, with the organisation's permission. That one fact explains the certificate, the bypass list, the cost and the legal questions in the rest of this page.

The two sessions

  1. A client in service VPN 10 opens a TCP connection to a web server and sends a TLS ClientHello that names the site.
  2. The WAN Edge intercepts it and completes a TLS session with the client itself. To do that, it creates a certificate for the requested site name and signs it with the organisation's CA key.
  3. The edge opens a separate TLS session to the real server and checks the server's own certificate.
  4. Between the two sessions the data is in clear text on the router. The inspection features (IPS, URL filtering, file scanning) work on it here.
  5. The edge encrypts the data again in each direction and forwards it.

The client does not talk to the server directly. If you look at the certificate in the browser, the issuer is your own CA. That is the visible sign that the proxy is working, and it is also the reason clients must trust that CA.

The two sessions of a TLS proxy
The two sessions of a TLS proxyWithout a proxy, the edge cannot read encrypted web traffic, so IPS, URL filtering and AMP see only ciphertext. With the TLS proxy, BR-01 ends the client's session using a certificate it signs with an enterprise CA that clients trust, reads the content, and opens a second session to the real server.ClientBR-01TLS proxyServerreal certificatesession 1session 2Client sees a certificatesigned by the enterprise CA(it must trust that CA)In the middle: plain textIPS, URL filtering and AMPcan look insideEdge checks the server'sreal certificatebefore it forwardsLeave out what should stay private or pinned, such as banking and some update services.

On small screens, swipe sideways or focus the diagram and use the arrow keys.

The edge needs a signing certificate the clients trust, some traffic should not be decrypted, and it costs processing power. Settle the legal and privacy questions before you roll it out.

Which certificate the edge signs with

The edge needs a CA certificate and its private key, so that it can sign the per-site certificates in step 2. The options are described here at a high level. How you load them in SD-WAN Manager depends on your release, so check the current documentation.

Which certificate the edge signs with
Which certificate the edge signs withOption; How it works; Where it fits. Enterprise CA signing certificate: The organisation's own PKI issues a CA certificate for the edge. Clients already trust the enterprise root, so no extra trust step is needed Production. The edge key is sensitive: treat it like any other CA key Self-signed CA on the edge: The edge uses a certificate it generates or you generate. You must distribute that certificate to every client yourself Labs and tests. Harder to manage and renew at scaleOptionHow it worksWhere it fitsEnterprise CA signingcertificateThe organisation's own PKI issues aCA certificate for the edge. Clientsalready trust the enterprise root, sono extra trust step is neededProduction. The edge key issensitive: treat it like any other CAkeySelf-signed CA on theedgeThe edge uses a certificate itgenerates or you generate. You mustdistribute that certificate to everyclient yourselfLabs and tests. Harder to manage andrenew at scale

On small screens, swipe sideways or focus the diagram and use the arrow keys.

Read each row across: the left box names the item, the others describe it.

Whichever you use, the client trust step is yours. Managed laptops usually receive the CA certificate through group policy or a device-management tool. Phones, printers, IoT devices and guest devices often cannot be given it, which is one reason they are bypassed.

What to decrypt and what to leave alone

Decrypting everything is rarely the right answer. A practical policy starts from the traffic that other controls need to inspect, and excludes the rest.

What to decrypt and what to leave alone
What to decrypt and what to leave aloneTraffic; Usual decision; Reason. General web browsing from managed laptops: Decrypt This is where web threats and downloads arrive Banking, health and similar privacy-sensitive categories: Bypass Privacy and legal exposure outweigh the inspection benefit Applications that pin certificates: Bypass They expect one specific server certificate and refuse the proxy's, so they stop working Internal services and private PKI: Usually bypass Already inside the organisation; the proxy may not trust the private CA that signed them Guest VPN 30 devices: Usually bypass The devices do not trust your CA Point-of-sale VPN 40 (example): Decide with the compliance team Payment data is regulated and the application may pin certificatesTrafficUsual decisionReasonGeneral web browsingfrom managed laptopsDecryptThis is where web threats anddownloads arriveBanking, health andsimilarprivacy-sensitivecategoriesBypassPrivacy and legal exposure outweighthe inspection benefitApplications that pincertificatesBypassThey expect one specific servercertificate and refuse the proxy's,so they stop workingInternal services andprivate PKIUsually bypassAlready inside the organisation; theproxy may not trust the private CAthat signed themGuest VPN 30 devicesUsually bypassThe devices do not trust your CAPoint-of-sale VPN 40(example)Decide with the compliance teamPayment data is regulated and theapplication may pin certificates

On small screens, swipe sideways or focus the diagram and use the arrow keys.

Read each row across: the left box names the item, the others describe it.

Site IDs and VPN numbers here are examples from the lab. The decision logic is what carries over.

Checking the server's certificate

Because the edge now makes the connection to the server, the edge is the one that must decide whether the server's certificate is acceptable. The user's browser can no longer judge it, because it only sees the proxy's certificate. If the server certificate is expired, self-signed, issued by an untrusted CA or for the wrong name, there are two choices:

  • Block. Safer. Users may complain about internal or partner sites with sloppy certificates.
  • Pass. Convenient, but the user loses the warning they would normally have seen. A risky site can look fine.

This is a design decision, not a technical default to accept. Check which behaviours and keywords your release offers, and write down the choice and who approved it.

What it costs

Decryption is the most demanding inspection task on the router. The edge performs two TLS handshakes per connection and encrypts and decrypts the data on top of the inspection itself. Expect higher CPU use, a little more latency per new connection and lower throughput than with inspection that does not decrypt. How much depends on the platform, the release and the traffic mix, so no figure is given here. Two things to check in the current platform documentation:

  • whether your WAN Edge model supports the TLS proxy at all, and with what resources assigned to the security container or service;
  • what throughput the vendor quotes with the proxy on, and under which test conditions.

Size from that data and from a trial, not from the datasheet figure for plain forwarding.

What it cannot proxy

  • TLS versions and ciphers the proxy does not support. Such connections cannot be decrypted. The policy decides whether they pass or are dropped. Check the supported versions in your release.
  • QUIC and HTTP/3. These run over UDP, usually port 443. A TCP-based proxy does not see them, so browsers that use QUIC can slip past decryption. Many designs block QUIC towards the internet so that browsers fall back to TCP and TLS, where the proxy works.
  • Certificate-pinned applications. They fail when proxied. Bypass them.
  • Mutual TLS (client certificates). The proxy cannot present the client's certificate to the server, so these connections generally need a bypass.
Why does blocking QUIC help?

A browser tries QUIC first and falls back to TCP if it fails. If the firewall drops UDP 443 to the internet, the browser quickly uses HTTPS over TCP instead, and the proxy can see it. Blocking is a design choice with a side effect: sites run slightly slower for a moment on the first visit. Test it with your own users before rolling it out.

Legal and privacy questions to settle first

Decryption lets the organisation read employees' web sessions, including passwords typed on sites it did not intend to monitor. Before deployment, get advice on at least these points:

  • whether staff must be told, and where (policy, contract, a banner);
  • which categories local rules say must not be decrypted, and who holds the logs;
  • how regulated data, such as card or health data, is handled when it passes through the proxy;
  • who may access decrypted data and for how long it is kept.

This page gives no legal advice. The rules differ by country and by industry.

Rolling it out

  1. Distribute the CA certificate to managed devices first, and confirm browsers on them trust it.
  2. Start with a small pilot group in one service VPN at one site, for example a few users at BR-01.
  3. Build the bypass list before the pilot, then add to it from what the pilot shows. Keep it in a reviewed document, not only in the configuration.
  4. Watch for failures: new certificate errors, applications that stop, and a rise in tickets after the change.
  5. Extend in stages. Watch router CPU and memory at each step.
  6. Put the CA certificate expiry date in a calendar with a renewal task well ahead. An expired signing certificate gives every decrypted user a warning at once.

Checking that it is working

The exact commands and counters differ between releases, so this lesson avoids guessing keywords. Check in this order:

  1. In SD-WAN Manager, confirm that the security policy with the TLS proxy is attached to the device template of the router, and that the template pushed successfully.
  2. Confirm the router shows the security service as running. In the platform documentation, find the show command for the inspection service state in your release.
  3. On a test client, open an HTTPS site that is in the decrypt scope. In the browser, check that the certificate issuer is your CA.
  4. Open a site on the bypass list. The issuer must be the real public CA.
  5. Review the router logs and the Manager monitoring pages for decryption failures and for the reason (unsupported version, certificate error, policy bypass).
Example output written for this lesson, simplified; real output has more fields and a different layout
BR-01#show utd engine standard status
Engine version      : (example)
Profile             : (example)
System memory       : (example)
Overall system status : Green
Example only. The command name is the kind of check to look for (is the inspection engine up?), and the fields shown are placeholders. Compare with the output on your own release before relying on either. A service that is not green usually means features that depend on it, including the proxy, are not working.
curl -vI https://www.example.com 2>&1 | grep -i "issuer"

Run from a test client, not the router. It prints the issuer of the certificate the client was given. With decryption on, the issuer is the organisation's CA. With a bypass, it is the public CA of the site.

When a site breaks after the proxy is switched on

  1. Does the problem affect only one site or application? Then suspect pinning, mutual TLS or an unsupported TLS version. Add it to the bypass list.
  2. Does it affect every site for one device? That device does not trust the CA.
  3. Does it affect every site for everyone? Check the CA certificate on the edge (expiry, chain) and the state of the inspection service.
  4. Is it slow rather than broken? Look at router CPU and the volume decrypted. Narrow the scope.

Once decryption works, the web features can use it. Continue with URL filtering, which gets full paths from decrypted HTTPS, and AMP, which can scan files in decrypted downloads.

Test yourself on the TLS proxy

Predict · scenario 1

After the TLS proxy is enabled, managed laptops browse normally, but a guest phone shows a certificate warning on every HTTPS site. Why?

Predict · scenario 2

A banking application works from the browser but its mobile app stops working after decryption starts. What is the most likely cause and the usual fix?

Predict · scenario 3

Decryption is on, but a test shows some HTTPS downloads are not inspected. The users' browsers support HTTP/3. What is a likely reason, and a common design response?

Predict · scenario 4

The edge's view of an expired server certificate matters because:

FAQ

Why do users see a certificate warning after the proxy is switched on?
The proxy presents a certificate signed by the organisation's CA, not by a public CA. If the device does not trust that CA, the browser warns. Managed devices get the CA certificate through device management. Unmanaged devices, such as guest phones, do not have it, so they are normally left out of decryption.
Does the TLS proxy decrypt everything?
Only what the policy selects. A sensible design decrypts traffic that other features need to inspect and bypasses categories with privacy or legal risk, applications that break, and internal services. Anything the proxy cannot handle is passed through or blocked, depending on the design.
Is it legal to decrypt employees' traffic?
It depends on the country, the data and the agreements in place. Notifying staff, limiting decryption of sensitive categories and handling regulated data carefully are common concerns. This lesson is not legal advice: ask your legal or privacy team before switching it on.