Zebra cloud print and certificate handshake support expert

Joe B.

Reviewed for technical accuracy

Specialities: Zebra Link-OS printers, Zebra Cloud Connect, SSL/TLS certificate handshake, PrintSecure, mutual TLS, stuck “pending” cloud print jobs

Fix “Zebra cloud print job stuck ‘pending’ — cert handshake” by repairing TLS trust, updating printer certificates, and clearing stalled cloud queues

Technician avatar Technician
Hey there — we can definitely help with a Zebra cloud print job stuck on “pending”. When jobs line up in your cloud UI but never leave the pending status, and logs mention certificate handshake failures or TLS handshake error, the printer usually isn’t allowed to talk securely to the cloud endpoint.

With Zebra Cloud Connect or WebLink-style cloud printing, the printer and server must trust each other’s SSL/TLS certificates. If the server cert is expired, the root CA is missing, or the printer’s own client certificate is invalid, the cloud print job looks “accepted” but stays stuck as pending in the Zebra cloud print queue instead of actually printing.

We’ll track down exactly where the cert handshake is failing and fix the trust chain so jobs move from pending to printed again.
Customer
That sounds like what we’re seeing. We have several Link-OS Zebra printers registered through Zebra Cloud Connect to a cloud app. Jobs hit the queue, but every Zebra cloud print job stays “pending” forever with no error on the front panel. In the connector logs we see “SSL certificate problem” and “TLS handshake failed”. I’m not sure if we broke something on the printer, in the cloud connector, or on the HTTPS endpoint.
Technician avatar Technician
That’s a textbook Zebra cloud print “pending” due to cert handshake scenario. The sequence is roughly:

1) Your cloud app creates a job and marks it as ready — that’s why you see it in the UI.
2) The Zebra Cloud Connect / WebLink client on the printer tries to open an HTTPS or WSS connection back to the cloud.
3) During the SSL/TLS handshake, the printer checks the server’s certificate chain and the server may validate the printer’s client certificate.
4) If anything in that chain fails — wrong hostname, expired cert, missing root CA, unsupported TLS version — the secure session is never established, so the job remains stuck as pending rather than “printing”.

The printers themselves are fine; they’re just refusing to talk to something they don’t trust. We need to find out whether the problem is the server certificate, the printer’s installed certificates, or a mismatch in what each side expects.
Customer
We did recently swap to a new wildcard certificate on the cloud side, and I don’t think we updated anything on the printers. Could that alone make every Zebra cloud print job stuck in pending? The error mentions “certificate not trusted” and “unknown CA” in some of the logs.
Technician avatar Technician
Yes, that would absolutely do it. Zebra’s SSL/TLS certificate errors documentation notes that a common cause of handshake failures is a missing or incorrect Zebra Certificate Authority (CA) or server certificate on one end of the connection. If you changed your public certificate and intermediate chain but didn’t update the trusted CA store on the printers, they’ll treat the new server as untrusted and fail the handshake, leaving jobs stuck in pending.

Quick fix path:
1) Export the correct root CA and intermediate certificates that sign your new wildcard cert.
2) Import that CA chain into each Zebra Link-OS printer using Web UI, ZPL, or a management tool (Printer Profile Manager, MDM, etc.).
3) Confirm in the printer’s security settings or PrintSecure profile that the new CA is trusted for outbound HTTPS/WebLink connections.

Once the printer trusts the new certificate chain, the TLS handshake should succeed and the Zebra cloud print jobs will move from “pending” to “printing” automatically.
Customer
That explains the trust issue. We’re also using mutual TLS for some printers, where the printer presents a client certificate to our cloud. Could an expired client cert on the Zebra side also cause this “cloud print job stuck pending” behavior?
Technician avatar Technician
Definitely. In a mutual TLS (mTLS) setup, the printer has its own device certificate and private key. During the handshake, the server validates that client certificate against a trusted CA list. If the printer’s client certificate is expired, revoked, or signed by a CA your server no longer trusts, the server will abort the TLS handshake.

From your side it looks like:
• Cloud UI: jobs accepted but never progress beyond pending.
• Logs: “TLS handshake error”, “bad certificate” or similar messages.

On the printer or in your PrintSecure / security profile, we’d check:
1) The validity dates of the installed client cert.
2) That the device certificate’s Common Name or SAN matches what the server expects (device ID, hostname, etc.).
3) That the server still trusts the CA that issued the printer certificate.

If anything is off, we regenerate the client cert, deploy it to the Zebra printer, and make sure the server trusts that CA so the certificate handshake completes correctly.
Customer
Good to know. One thing that confuses me is that test jobs sent over raw TCP or USB work fine. It’s only when we use Zebra cloud print over HTTPS/WebLink that jobs get stuck as “pending”. Is that normal for a certificate issue?
Technician avatar Technician
Yep, that actually helps confirm the diagnosis. Local jobs over USB, parallel, or plain TCP/IP don’t use SSL/TLS at all — they’re just sending ZPL or print data straight to the printer. So they keep working even if all your TLS certificates are broken.

Cloud workflows like Zebra Cloud Connect, WebLink, or HTTPS-based label printing rely on a full SSL/TLS handshake every time the printer connects to the cloud. That’s where expired certs, hostname mismatches, or missing CA certificates show up and cause the “pending” cloud print job symptom.

In other words: local print success just proves the print engine is fine. The real issue is higher up — in secure connectivity and certificate configuration between your Zebra printer and the cloud service.
Customer
Makes sense. What’s the best way to actually see the TLS handshake error details from the Zebra side? Right now our app just says “connection failed” and everything stays in the pending state.
Technician avatar Technician
Great question — the detailed reason for a Zebra SSL/TLS handshake error is usually visible in:

• The printer’s WebLink / Cloud Connect log (via the web interface or a diagnostic printout).
• Syslog or a remote log server, if you’ve pointed the printer there.
• The cloud connector or gateway logs, which often show “certificate verify failed”, “unknown CA”, or “certificate expired”.

Zebra’s documentation on SSL/TLS certificate errors breaks down common codes like “certificate has expired”, “self-signed certificate”, and “unable to get local issuer certificate”, which map straight to what you’ll see in your logs.

If you’d like, we can step through grabbing one of those logs live, identify exactly which certificate handshake is failing, and then update the right CA or client certificate so Zebra cloud print jobs stop getting stuck in pending.
Customer
Once we fix the certificate chain and client certs, is there anything else that typically keeps Zebra cloud print jobs pending? I want to make sure we don’t miss a setting like TLS versions or ciphers.
Technician avatar Technician
Good thinking. After certificates, the next most common causes for a Zebra cloud print “pending” state are:

• TLS version mismatch: your cloud requires TLS 1.2+ while the printer is locked to an older protocol, or vice versa.
• Unsupported cipher suites: very locked-down servers may disable ciphers the Zebra printer prefers, causing the TLS handshake to fail.
• Wrong system time: if the printer’s clock is far off, certificates can appear “not yet valid” or “expired”.
• Stuck connector queue: after multiple failures, some cloud connectors need a restart or queue flush before new jobs move past pending.

As part of the fix we usually:
1) Confirm the printer’s date/time (via NTP or manual set).
2) Match TLS version and cipher requirements between your Zebra PrintSecure policy and the server.
3) Restart or reset the Zebra cloud connector / WebLink session so the queue can re-sync and re-attempt jobs with the new settings.
Customer
Got it. For our operations team, could you outline clear steps they can follow anytime they see a Zebra cloud print job stuck “pending” with a suspected certificate handshake issue?
Technician avatar Technician
Absolutely — here’s a simple playbook you can turn into an SOP for Zebra cloud print job stuck “pending” — cert handshake cases:

1) Check logs: Grab Zebra cloud / WebLink logs and confirm error text like “certificate has expired”, “unknown CA”, or “TLS handshake failed”.
2) Validate server cert: On the cloud endpoint, verify the HTTPS certificate is valid, not expired, and matches the host name your Zebra printers connect to.
3) Update printer trust store: Import the correct root CA and intermediate certs into each Zebra printer so it trusts the server chain.
4) Refresh client certs (if mTLS): For mutual TLS, regenerate and deploy device certificates to printers and confirm the server trusts the issuing CA.
5) Align TLS settings: Make sure TLS version and cipher requirements are compatible between your PrintSecure policy and the server.
6) Sync time & restart cloud session: Fix printer date/time if needed, then restart the Zebra cloud connector or WebLink service so pending jobs are retried.

Once those are in place, a Zebra cloud print queue that was stuck at “pending” because of certificate handshake problems usually starts draining within a few seconds. If you’d like help doing this live, open the chat and an expert will walk you through each step.
Customer
Perfect. Just to confirm: none of these changes affect the label formats themselves, right? We only want to fix the Zebra cloud print certificate handshake problem, not touch our ZPL templates.
Technician avatar Technician
Correct — everything we’ve covered lives in the security and connectivity layer, not in your label formats:

• Updating trusted CAs and device certificates only affects whether the TLS connection is allowed — your ZPL label content stays unchanged.
• Tweaking TLS versions or ciphers simply tells the printer and server how to secure the connection, not what to print.
• Restarting the Zebra cloud connector or clearing a stuck queue just replays existing jobs; it doesn’t modify the label data.

So you can safely fix Zebra cloud print jobs stuck on “pending” by repairing the certificate handshake and trust chain, while leaving your label templates, barcodes, and layouts exactly as they are. If you’d like a pair of eyes on your current setup, start a chat and an expert can review your certificates and PrintSecure policies in real time.

Quick answer: the accepted fix

Accepted fix when a Zebra cloud print job is stuck on “pending” with a certificate handshake error: validate the server’s HTTPS certificate, install the correct root CA and intermediate certificates on each Zebra printer, refresh any mutual TLS client certs, align TLS settings, then restart the cloud connector so jobs retried from the queue move from pending to printing.

Why Zebra cloud print jobs stay “pending” when TLS or certificates are misconfigured

When a Zebra cloud print job is stuck in pending status, the underlying problem is rarely the label format. Instead, the printer can’t finish the SSL/TLS handshake to the cloud endpoint, so it never pulls the job down to print. Common causes include an expired server certificate, a missing root CA on the printer, a hostname mismatch, or an invalid client certificate in a mutual TLS setup. From the cloud application’s perspective, the job looks “queued”, but from the Zebra printer’s point of view, the secure session failed, so the pending cloud print job never transitions to “printing”. Fixing the certificate chain and TLS policy on both ends is what actually clears the queue.

How to verify your Zebra cloud print certificate handshake is fixed

After updating CAs and device certificates, you’ll want to confirm that Zebra cloud print jobs no longer get stuck on “pending”. Start by restarting or reconnecting the Zebra Cloud Connect / WebLink client, then send a small test label from your cloud app. Watch the job status change from pending → printing → complete in the UI, and confirm the label comes out on the correct printer. Check logs on both sides to make sure there are no new TLS handshake errors or certificate warnings. If test jobs print cleanly without errors, you can be confident that your Zebra cloud print certificate handshake and trust chain are correctly configured.

Zebra cloud print job stuck “pending” — quick certificate tips

Most “pending” jobs in Zebra cloud print are blocked by TLS trust, not by the label format.

Fastest path to a fix: verify your cloud server’s HTTPS certificate, then import the matching root CA and intermediate certs into your Zebra printers so they trust the endpoint. For setups using mutual TLS, deploy fresh device certificates to the printers and confirm the server trusts their issuing CA. Combine that with correct TLS versions and cipher suites, and your Zebra cloud print queue will stop piling up “pending” jobs and start delivering labels to the right devices in seconds.

Disclaimer: This information is AI-generated and intended for general guidance only. For advice specific to your Zebra printer models, cloud platform, and security requirements, please consult a verified expert on Whizz-Tech before making changes.

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FAQ

Why are my Zebra cloud print jobs always stuck on “pending”?

Most Zebra cloud print jobs stuck in pending are caused by SSL/TLS handshake failures between the printer and the cloud server. Expired server certificates, missing root CA certificates on the printer, or incompatible TLS versions prevent a secure connection, so jobs stay pending instead of printing.

How do I fix a certificate handshake error with Zebra Cloud Connect?

First, verify that your cloud server’s HTTPS certificate is valid and correctly chained. Then import the appropriate root and intermediate CA certificates into your Zebra printers and, if you use mutual TLS, deploy valid device certificates. Finally, restart the Zebra cloud connector so new jobs can complete the TLS handshake.

Can TLS version or cipher settings cause Zebra cloud jobs to stay pending?

Yes. If your Zebra printer is locked to certain TLS versions or cipher suites that the server does not accept (or vice versa), the TLS handshake will fail and cloud print jobs may remain in pending state. Aligning PrintSecure TLS policies with your server’s security policy is essential.

Do certificate fixes affect my Zebra label formats or ZPL templates?

No. Adjusting certificates, CAs, and TLS settings only changes how the printer connects securely to the cloud. Your ZPL label formats, barcodes, and layouts stay the same — you’re just allowing pending cloud print jobs to reach the printer again.

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