TLS connections to Oracle Database failing in Docker Desktop on macOS 26

[fraserhess]

Description

This is very niche. Our organization has legacy apps in Docker containers that connect to Oracle databases over TLS. The certificates are issued by our internal CA.

This has worked on our Apple silicon developer Macs for some time but has been broken after upgrading to macOS 26.x from macOS 15.7.2. After upgrade, the connections now fail with OCIError: ORA-29024: Certificate validation failure. The apps are not in question as we can reproduce the errors with sqlplus. After the developers brought this problem to me (I'm the Mac admin), I was able to recreate the issue in a lab computer: successful connection from the container on macOS 15.7.2, upgrade to 26.2 and immediately fail the test.

I'll list more of what we've tested below, but where Docker experts might be able to shine light on this is that we have able to workaround the issue by either disabling Rosetta, or switching to Docker VMM.

Tested on:

• Every release of Docker Desktop 4.55-4.59.1
• Every build of macOS 26.2-26.3b3
• On-premises and over VPN

Other tests:

• Packet capture of the connection, extraction of the certificates, ran against openssl verify - successful
• Extracting the Oracle wallet (source of root certificates trust) from the container and testing with another system - successful
• Connecting with openssl s_client in and out of the container - successful
• Disabling macOS 26 post quantum TLS changes

It would be worthwhile to better understand the differences between the use of Apple Virtualization and Docker VMM, and how amd64 is emulated without Rosetta.

Reproduce

While I've tried to spell out the problem in detail above, I can't really give reproducible steps as I don't have a public Oracle DB with TLS.

Expected behavior

No response

docker version

% docker version
Client:
 Version:           29.2.0
 API version:       1.53
 Go version:        go1.25.6
 Git commit:        0b9d198
 Built:             Mon Jan 26 19:25:13 2026
 OS/Arch:           darwin/arm64
 Context:           desktop-linux

Server: Docker Desktop 4.59.1 (217750)
 Engine:
  Version:          29.2.0
  API version:      1.53 (minimum version 1.44)
  Go version:       go1.25.6
  Git commit:       9c62384
  Built:            Mon Jan 26 19:25:48 2026
  OS/Arch:          linux/arm64
  Experimental:     false
 containerd:
  Version:          v2.2.1
  GitCommit:        dea7da592f5d1d2b7755e3a161be07f43fad8f75
 runc:
  Version:          1.3.4
  GitCommit:        v1.3.4-0-gd6d73eb8
 docker-init:
  Version:          0.19.0
  GitCommit:        de40ad0

docker info

% docker info
Client:
 Version:    29.2.0
 Context:    desktop-linux
 Debug Mode: false
 Plugins:
  ai: Docker AI Agent - Ask Gordon (Docker Inc.)
    Version:  v1.17.2
    Path:     /Users/hessf/.docker/cli-plugins/docker-ai
  buildx: Docker Buildx (Docker Inc.)
    Version:  v0.31.1-desktop.1
    Path:     /Users/hessf/.docker/cli-plugins/docker-buildx
  compose: Docker Compose (Docker Inc.)
    Version:  v5.0.2
    Path:     /Users/hessf/.docker/cli-plugins/docker-compose
  debug: Get a shell into any image or container (Docker Inc.)
    Version:  0.0.47
    Path:     /Users/hessf/.docker/cli-plugins/docker-debug
  desktop: Docker Desktop commands (Docker Inc.)
    Version:  v0.2.0
    Path:     /Users/hessf/.docker/cli-plugins/docker-desktop
  extension: Manages Docker extensions (Docker Inc.)
    Version:  v0.2.31
    Path:     /Users/hessf/.docker/cli-plugins/docker-extension
  init: Creates Docker-related starter files for your project (Docker Inc.)
    Version:  v1.4.0
    Path:     /Users/hessf/.docker/cli-plugins/docker-init
  mcp: Docker MCP Plugin (Docker Inc.)
    Version:  v0.37.0
    Path:     /Users/hessf/.docker/cli-plugins/docker-mcp
  model: Docker Model Runner (Docker Inc.)
    Version:  v1.0.8
    Path:     /Users/hessf/.docker/cli-plugins/docker-model
  offload: Docker Offload (Docker Inc.)
    Version:  v0.5.41
    Path:     /Users/hessf/.docker/cli-plugins/docker-offload
  pass: Docker Pass Secrets Manager Plugin (beta) (Docker Inc.)
    Version:  v0.0.24
    Path:     /Users/hessf/.docker/cli-plugins/docker-pass
  sandbox: Docker Sandbox (Docker Inc.)
    Version:  v0.10.1
    Path:     /Users/hessf/.docker/cli-plugins/docker-sandbox
  sbom: View the packaged-based Software Bill Of Materials (SBOM) for an image (Anchore Inc.)
    Version:  0.6.0
    Path:     /Users/hessf/.docker/cli-plugins/docker-sbom
  scout: Docker Scout (Docker Inc.)
    Version:  v1.19.0
    Path:     /Users/hessf/.docker/cli-plugins/docker-scout

Server:
 Containers: 2
  Running: 2
  Paused: 0
  Stopped: 0
 Images: 2
 Server Version: 29.2.0
 Storage Driver: overlay2
  Backing Filesystem: extfs
  Supports d_type: true
  Using metacopy: false
  Native Overlay Diff: true
  userxattr: false
 Logging Driver: json-file
 Cgroup Driver: cgroupfs
 Cgroup Version: 2
 Plugins:
  Volume: local
  Network: bridge host ipvlan macvlan null overlay
  Log: awslogs fluentd gcplogs gelf journald json-file local splunk syslog
 CDI spec directories:
  /etc/cdi
  /var/run/cdi
 Discovered Devices:
  cdi: docker.com/gpu=webgpu
 Swarm: inactive
 Runtimes: io.containerd.runc.v2 runc
 Default Runtime: runc
 Init Binary: docker-init
 containerd version: dea7da592f5d1d2b7755e3a161be07f43fad8f75
 runc version: v1.3.4-0-gd6d73eb8
 init version: de40ad0
 Security Options:
  seccomp
   Profile: builtin
  cgroupns
 Kernel Version: 6.12.67-linuxkit
 Operating System: Docker Desktop
 OSType: linux
 Architecture: aarch64
 CPUs: 8
 Total Memory: 3.827GiB
 Name: docker-desktop
 ID: 16ab7eef-4810-45b5-b8f9-a80157097782
 Docker Root Dir: /var/lib/docker
 Debug Mode: false
 HTTP Proxy: http.docker.internal:3128
 HTTPS Proxy: http.docker.internal:3128
 No Proxy: hubproxy.docker.internal
 Labels:
  com.docker.desktop.address=unix:///Users/hessf/Library/Containers/com.docker.docker/Data/docker-cli.sock
 Experimental: false
 Insecure Registries:
  hubproxy.docker.internal:5555
  127.0.0.0/8
  ::1/128
 Live Restore Enabled: false
 Firewall Backend: iptables

Diagnostics ID

E77BC9D7-7ECB-4618-A83E-AC917C526D95/20260204004332

Additional Info

No response