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“Sending with winhttp failed” is a transport symptom, not a diagnosis. The HRESULT that follows it, the URL being contacted, the deployment phase, and the surrounding log lines determine whether you are dealing with DNS, routing, firewall or proxy behavior, TLS and certificates, a missing WinPE driver, content distribution, Windows Setup, or only a failed status-message submission.
The most specific documented case is 0x80072f8f with WINHTTP_CALLBACK_STATUS_FLAG_INVALID_CA when PKI HTTPS media is created at a central administration site that does not have the root CA configured. In that case, recreate the bootable or prestaged media at a primary site. That remedy does not apply to every WinHTTP error.
Start by locating the failure
First record the last successful task-sequence step and whether the computer is in Windows PE or the installed operating system. The same WinHTTP text can appear during different operations.
| What you see | Most likely area |
|---|---|
| PXE or media starts, but the wizard cannot retrieve policy | WinPE networking, management-point discovery, DNS, HTTPS trust, client identity, site assignment, or media configuration |
| Policy is retrieved but content will not download | Distribution-point selection, boundaries, content distribution, ports, IIS, firewall, or connectivity |
| Failure at Setup Windows and ConfigMgr | Windows Setup, client staging, the OSD setup hook, or the reboot transition |
| Failure after reboot into Windows | Full-OS network drivers, DNS, CCMSetup, client location, or task-sequence resumption |
Capture the complete HRESULT, target FQDN and port, URL path, task-sequence phase, and the preceding and following 20–50 lines of smsts.log. Also note whether the problem affects one device, one hardware model, one subnet, or every deployment.
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Find the right logs
The active smsts.log location changes during deployment. The read-only task-sequence variable _SMSTSLogPath reports the current directory; Microsoft documents that variable at Task-sequence variables.
| Phase | Primary location |
|---|---|
| WinPE before Format and Partition Disk | X:WindowsTempSMSTSLogsmsts.log |
| WinPE after Format and Partition Disk | X:SMSTSLogsmsts.log |
| Disk available, before the new client is installed | C:_SMSTaskSequenceLogsSMSTSLogsmsts.log |
| Full Windows after the client is installed | C:WindowsCCMLogsSMSTSLogsmsts.log |
| After task-sequence completion | C:WindowsCCMLogssmsts.log |
Collect related logs according to the operation:
C:WindowsCCMSetupLogsccmsetup.logandclient.msi.logfor client installation.C:WindowsPanthersetupact.logandsetuperr.logfor Windows Setup; before the installed disk is available, checkX:WindowsPanther.C:WindowsINFsetupapi.dev.logfor device and driver installation.LocationServices.log,ClientLocation.log,PolicyAgent.log, andPolicyEvaluator.logfor location, assignment, and policy.CAS.log,ContentTransferManager.log, andDataTransferService.logfor content location and transfer.smspxe.logon the distribution point for PXE-service activity.
Microsoft identifies setupact.log as the primary Windows Setup activity log and documents task-sequence log paths at Configuration Manager log files and Windows Setup logs at Windows Setup log files and event logs.
Read the HRESULT in context
| Value | Likely direction in this scenario | Check |
|---|---|---|
0x80072f8f |
TLS, certificate, secure-channel, or trust-chain failure | CA chain, MP certificate, system time, media-generation site, HTTPS configuration, and the exact secure-failure flags |
0x80072ee7 |
Host-name resolution failure | WinPE DNS, DHCP options, suffix/search list, split DNS, VLAN or VPN routing, and the MP FQDN |
0x80072ee2 |
Timeout or unreachable service | Routing, ACLs, firewall, proxy, MP/DP health, and connectivity during reboot |
0x80072efd |
Failure to establish the requested connection | Listening port, IIS binding, configured HTTP/HTTPS port, firewall, and DP/MP configuration |
0x80004005 |
Generic error shown by the wizard | Use the underlying WinHTTP, certificate, DNS, client, or policy error in smsts.log |
These are investigation branches, not universal translations. Microsoft Q&A associates 0x80072ee7 with an unresolved server name or address: Q&A discussion.
The documented 0x80072f8f PKI-media case
Recognize the pattern
Microsoft documents a bootable or prestaged-media scenario in which the wizard remains at Retrieving policy for this computer, later shows 0x80004005, and smsts.log contains entries such as:
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- Compatible with Windows 8.1 or higher, Mac OS
WINHTTP_CALLBACK_STATUS_SECURE_FAILURE Encountered
WINHTTP_CALLBACK_STATUS_FLAG_INVALID_CA is set
Error. Received 0x80072f8f from WinHttpSendRequest
Sending with winhttp failed; 80072f8f
Failed to get client identity
SyncTimeWithMP() failed
Failed to query Management Point locatorThe environment uses PKI and HTTPS management points. Media was generated at the central administration site, while the root CA was configured at a primary site. The media therefore lacks the CA information needed to validate the management-point certificate.
Apply the supported remedy
Create the bootable or prestaged media at a primary site, not at the central administration site. Microsoft states that dynamic media can be created at any site. See the complete case and resolution at Sending with WinHTTP failed with 0x80072f8f.
Do not recreate media solely because the code is 80072f8f. First confirm that the URL is an HTTPS management point, PKI is in use, the log contains certificate or invalid-CA indicators, and the affected media was generated in the configuration described above. A bad system clock, expired certificate, incomplete chain, wrong subject/SAN, or incorrect certificate usage needs certificate remediation instead.
Separate Windows PE from full Windows
When the failure is in WinPE
WinPE must have an address, DNS and gateway information, a working NIC driver, and trust for the management point. From a command prompt, run:
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ipconfig /all
wpeutil InitializeNetwork
nslookup managementpoint.example.comIf PowerShell is included in the boot image, test the actual service rather than relying on ICMP:
Resolve-DnsName managementpoint.example.com
Test-NetConnection managementpoint.example.com -Port 443Replace the hostname and port with those shown in the log or configured for the site. A failed ping does not prove HTTPS is unavailable because ICMP may be blocked.
For WinPE failures, verify the boot image contains the correct network driver, DHCP supplied DNS and gateway settings, the MP FQDN resolves from that VLAN, the configured port is reachable, the root CA is available where required, and the system clock is close enough for certificate validation.
When the failure is after reboot
Confirm that Windows received a usable network driver and did not lose its adapter or change from wired to wireless. Then inspect Panther logs, ccmsetup.log, and the new full-Windows smsts.log. Check whether a proxy, VPN, firewall, or security product blocks the MP, and whether the client is trying to resume before CCMSetup is ready.
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HTTPS and certificate checks
- On the management point, verify that the certificate is valid, unexpired, intended for server authentication, has a subject or SAN matching the FQDN, and presents a complete chain.
- On WinPE and the installed OS, verify trust for the issuing and root CAs. Do not assume that a CA trusted by a domain-joined Windows installation is automatically present in boot media.
- Where mutual certificate authentication is required, confirm a client certificate with its private key and required EKUs is available.
- Check system time, IIS bindings, MP communication mode, and the port used by the request.
In the Microsoft case, WinHTTP reports an invalid CA while requesting management-point identity. That detailed flag is more useful than the generic HRESULT.
DNS, routing, firewall, and proxy troubleshooting
For 0x80072ee7 or messages such as unknown host, gethostbyname failed, or “server name or address could not be resolved,” check, in order:
- Whether the failing environment has a valid DNS server.
- DHCP scope options, DNS suffix/search list, and gateway settings.
- VLAN, boundary, ACL, split-DNS, and VPN routing.
- Whether the MP name resolves to an address reachable from that network.
- Whether the task sequence uses a name available only on corporate DNS.
For 0x80072ee2, investigate timeouts caused by routing, firewalls, proxies, intermittent wireless, service load, or network loss during reboot. For 0x80072efd, verify that the requested service is listening on the expected port and that IIS and firewall rules match the ConfigMgr configuration.
A historical support case recorded HTTPS distribution-point content requests going to port 443 even though the DP used a nondefault port. It applies to older System Center Configuration Manager versions and should not be assumed to describe every current branch: Microsoft support article.
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When the problem is a distribution point
If the failing URL is a DP content path rather than an MP identity or policy endpoint, focus on content and location. Confirm that the package, boot image, and client package are distributed successfully; the device’s boundary group has an appropriate DP; the DP is reachable on its configured HTTP or HTTPS port; IIS bindings and certificates are correct; and the device did not change networks during the task sequence.
Use LocationServices.log for location decisions and CAS.log, ContentTransferManager.log, and DataTransferService.log for content selection and transfer. An MP request such as a client-identity or policy endpoint points to a different troubleshooting path than a DP content request.
Diagnose Setup Windows and ConfigMgr separately
This required step begins in Windows PE, stages and installs the Configuration Manager client, installs the OSD setup hook, reboots into the new operating system, and enables task-sequence continuation. It is not merely a network step. Microsoft states that an error in this step fails the task sequence even when Continue on error is enabled; see Task-sequence steps.
Check the transition logs
In smsts.log, search for:
OSDSetupWindows
OSDSetupHook
CCMSetup
TSMBootstrapThen inspect:
X:WindowsPantherorC:WindowsPanther, especiallysetupact.logandsetuperr.log.C:WindowsCCMSetupLogsccmsetup.logandclient.msi.log.C:WindowsINFsetupapi.dev.logfor post-reboot device failures.
Verify the client package is distributed to the relevant DPs, the selected package is compatible and not an invalid preproduction client, installation properties are correct, and the client can locate its site and MP after reboot. For internet-based Microsoft Entra-joined or token-authentication scenarios, the CCMHOSTNAME property may be required in this step.
Decide whether the WinHTTP line is fatal
Find the operation immediately before the error. Terms such as Getting MP time information, Requesting client identity, QueryMPLocator, Failed to get policy, or DownloadContent indicate a dependency required for progress. A line following Send status message may only mean that reporting failed; the task sequence can sometimes continue.
Do not classify the message from its wording alone. The failed operation and the next successful or failed task-sequence action establish severity.
Quick Recap
A practical decision procedure
- Identify the phase: policy retrieval, content download, Setup Windows and ConfigMgr, or post-reboot continuation.
- Extract the request: HRESULT, FQDN, port, URL path, MP or DP, HTTP or HTTPS, and whether a client certificate was presented.
- Test from the failing environment: use
ipconfigandnslookupin WinPE; useResolve-DnsNameandTest-NetConnectionin full Windows. - Follow evidence for certificates: investigate CA, TLS, time, and certificate details only when the log shows secure-failure indicators.
- Compare scope: site-wide failures suggest infrastructure; one subnet suggests DNS, DHCP, routing, firewall, or boundaries; one hardware model suggests drivers; media-only failures suggest embedded configuration or stale media; post-reboot failures suggest full-OS networking or CCMSetup.
- Remediate after isolation: recreate media at the appropriate site, update boot-image drivers, redistribute content, correct DNS or firewall rules, repair certificates or bindings, or update the task-sequence client package.
What to include when escalating
- Complete HRESULT and the full URL, hostname, and port.
- Deployment type: PXE, bootable media, prestaged media, or in-place upgrade.
- Last successful step and exact phase: WinPE or full Windows.
- Relevant
smsts.logexcerpt plus MP/DP and client logs. - PKI, HTTPS, enhanced-HTTP, proxy, VPN, and certificate details.
- Affected hardware models, subnets, boundaries, and whether the issue is universal.
- Recent changes to media, boot images, drivers, certificates, MP/DP settings, DNS, or firewall rules.
Prevent repeat failures
- Retest bootable and prestaged media after PKI, MP, site, or certificate changes.
- Keep boot images and model-specific network drivers current.
- Validate DNS and the actual MP/DP ports from every deployment VLAN.
- Maintain a known-good test deployment and a test device on each important network path.
- Monitor MP and DP health and content distribution before production imaging.
- Capture task-sequence logs automatically when a deployment fails.
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