diff --git a/integration/images/volume-copy-up/Dockerfile b/integration/images/volume-copy-up/Dockerfile
index 24ce3f454..38471736a 100644
--- a/integration/images/volume-copy-up/Dockerfile
+++ b/integration/images/volume-copy-up/Dockerfile
@@ -16,4 +16,19 @@ ARG BASE
 
 FROM $BASE
 RUN sh -c "mkdir /test_dir; echo test_content > /test_dir/test_file"
-VOLUME "/test_dir"
+RUN sh -c "mkdir -p /C:/weird_test_dir; echo test_content > /C:/weird_test_dir/weird_test_file"
+RUN sh -c "mkdir /:colon_prefixed; echo test_content > /:colon_prefixed/colon_prefixed_file"
+
+# We add a Windows style path here to ensure that for Linux, we don't mangle it in any way.
+# The C: drive letter gets special treatment on Windows and is stripped by WithVolumes(). The remaining
+# path is used to join with the volume mount point on the host. Colons are not allowed
+# in Windows paths except when delimiting the drive letter, but on Linux such paths are
+# perfectly valid and we must ensure we don't mutate them by accident.
+#
+# The C:/weird_test_dir volume is considered relative to "/" and will result in a mount point
+# situated at /C:/weird_test_dir.
+#
+# The "/:colon_prefixed" volume is meant to test that we don't ignore copying existing contents
+# to a volume containing a colon as the second character in the path on Linux, considering that
+# on Windows, we skip this operation for any non-C volume defined here.
+VOLUME ["/test_dir", "C:/weird_test_dir", "/:colon_prefixed"]
diff --git a/integration/images/volume-copy-up/Dockerfile_windows b/integration/images/volume-copy-up/Dockerfile_windows
index 5e57623f5..6299cbdb1 100644
--- a/integration/images/volume-copy-up/Dockerfile_windows
+++ b/integration/images/volume-copy-up/Dockerfile_windows
@@ -34,4 +34,10 @@ RUN mkdir C:\test_dir && \
     /bin/sh.exe -c "echo test_content > /test_dir/test_file"
 
 ENV PATH="C:\bin;C:\Windows\System32;C:\Windows;"
-VOLUME "C:/test_dir"
+
+# Add an extra volume under D: to test that WithVoumes() doesn't err out when dealing with
+# a non-C volume in WCOW.
+#
+# See:
+# https://github.com/containerd/containerd/issues/8171
+VOLUME ["C:/test_dir", "D:"]
diff --git a/integration/images/volume-copy-up/Makefile b/integration/images/volume-copy-up/Makefile
index cba817488..a77694f99 100644
--- a/integration/images/volume-copy-up/Makefile
+++ b/integration/images/volume-copy-up/Makefile
@@ -15,7 +15,7 @@
 all: build
 
 PROJ=ghcr.io/containerd
-VERSION=2.1
+VERSION=2.2
 IMAGE=$(PROJ)/volume-copy-up:$(VERSION)
 DOCKER_CERT_PATH ?= "$(HOME)/.docker"
 REMOTE_DOCKER_URL ?=