diff --git a/pkg/transfer/streaming/stream.go b/pkg/transfer/streaming/stream.go
index cf77cb8b5..061fd172d 100644
--- a/pkg/transfer/streaming/stream.go
+++ b/pkg/transfer/streaming/stream.go
@@ -164,7 +164,7 @@ func ReceiveStream(ctx context.Context, stream streaming.Stream) io.Reader {
 			}
 			anyType, err := stream.Recv()
 			if err != nil {
-				if errors.Is(err, io.EOF) {
+				if errors.Is(err, io.EOF) || errors.Is(err, context.Canceled) {
 					err = nil
 				} else {
 					err = fmt.Errorf("received failed: %w", err)
diff --git a/platforms/defaults_windows.go b/platforms/defaults_windows.go
index fd5756516..d10fa9012 100644
--- a/platforms/defaults_windows.go
+++ b/platforms/defaults_windows.go
@@ -22,6 +22,7 @@ import (
 	"strconv"
 	"strings"
 
+	"github.com/Microsoft/hcsshim/osversion"
 	specs "github.com/opencontainers/image-spec/specs-go/v1"
 	"golang.org/x/sys/windows"
 )
@@ -50,15 +51,36 @@ func (m windowsmatcher) Match(p specs.Platform) bool {
 	match := m.defaultMatcher.Match(p)
 
 	if match && m.OS == "windows" {
-		if strings.HasPrefix(p.OSVersion, m.osVersionPrefix) {
+		// HPC containers do not have OS version filled
+		if p.OSVersion == "" {
 			return true
 		}
-		return p.OSVersion == ""
+
+		hostOsVersion := GetOsVersion(m.osVersionPrefix)
+		ctrOsVersion := GetOsVersion(p.OSVersion)
+		return osversion.CheckHostAndContainerCompat(hostOsVersion, ctrOsVersion)
 	}
 
 	return match
 }
 
+func GetOsVersion(osVersionPrefix string) osversion.OSVersion {
+	parts := strings.Split(osVersionPrefix, ".")
+	if len(parts) < 3 {
+		return osversion.OSVersion{}
+	}
+
+	majorVersion, _ := strconv.Atoi(parts[0])
+	minorVersion, _ := strconv.Atoi(parts[1])
+	buildNumber, _ := strconv.Atoi(parts[2])
+
+	return osversion.OSVersion{
+		MajorVersion: uint8(majorVersion),
+		MinorVersion: uint8(minorVersion),
+		Build:        uint16(buildNumber),
+	}
+}
+
 // Less sorts matched platforms in front of other platforms.
 // For matched platforms, it puts platforms with larger revision
 // number in front.
diff --git a/platforms/defaults_windows_test.go b/platforms/defaults_windows_test.go
index 468438038..ab73ddda0 100644
--- a/platforms/defaults_windows_test.go
+++ b/platforms/defaults_windows_test.go
@@ -142,6 +142,110 @@ func TestMatchComparerMatch_WCOW(t *testing.T) {
 	}
 }
 
+// TestMatchComparerMatch_ABICheckWCOW checks windows platform matcher
+// behavior for stable ABI and non-stable ABI compliant versions
+func TestMatchComparerMatch_ABICheckWCOW(t *testing.T) {
+	platformWS2019 := imagespec.Platform{
+		Architecture: "amd64",
+		OS:           "windows",
+		OSVersion:    "10.0.17763",
+	}
+	platformWS2022 := imagespec.Platform{
+		Architecture: "amd64",
+		OS:           "windows",
+		OSVersion:    "10.0.20348",
+	}
+	platformWindows11 := imagespec.Platform{
+		Architecture: "amd64",
+		OS:           "windows",
+		OSVersion:    "10.0.22621",
+	}
+	matcherWS2019 := windowsmatcher{
+		Platform:        platformWS2019,
+		osVersionPrefix: platformWS2019.OSVersion,
+		defaultMatcher: &matcher{
+			Platform: Normalize(platformWS2019),
+		},
+	}
+	matcherWS2022 := windowsmatcher{
+		Platform:        platformWS2022,
+		osVersionPrefix: platformWS2022.OSVersion,
+		defaultMatcher: &matcher{
+			Platform: Normalize(platformWS2022),
+		},
+	}
+	matcherWindows11 := windowsmatcher{
+		Platform:        platformWindows11,
+		osVersionPrefix: platformWindows11.OSVersion,
+		defaultMatcher: &matcher{
+			Platform: Normalize(platformWindows11),
+		},
+	}
+
+	for _, test := range []struct {
+		hostPlatformMatcher windowsmatcher
+		testPlatform        imagespec.Platform
+		match               bool
+	}{
+		{
+			hostPlatformMatcher: matcherWS2019,
+			testPlatform: imagespec.Platform{
+				Architecture: "amd64",
+				OS:           "windows",
+				OSVersion:    "10.0.17763",
+			},
+			match: true,
+		},
+		{
+			hostPlatformMatcher: matcherWS2019,
+			testPlatform: imagespec.Platform{
+				Architecture: "amd64",
+				OS:           "windows",
+				OSVersion:    "10.0.20348",
+			},
+			match: false,
+		},
+		{
+			hostPlatformMatcher: matcherWS2022,
+			testPlatform: imagespec.Platform{
+				Architecture: "amd64",
+				OS:           "windows",
+				OSVersion:    "10.0.17763",
+			},
+			match: false,
+		},
+		{
+			hostPlatformMatcher: matcherWS2022,
+			testPlatform: imagespec.Platform{
+				Architecture: "amd64",
+				OS:           "windows",
+				OSVersion:    "10.0.20348",
+			},
+			match: true,
+		},
+		{
+			hostPlatformMatcher: matcherWindows11,
+			testPlatform: imagespec.Platform{
+				Architecture: "amd64",
+				OS:           "windows",
+				OSVersion:    "10.0.17763",
+			},
+			match: false,
+		},
+		{
+			hostPlatformMatcher: matcherWindows11,
+			testPlatform: imagespec.Platform{
+				Architecture: "amd64",
+				OS:           "windows",
+				OSVersion:    "10.0.20348",
+			},
+			match: true,
+		},
+	} {
+		assert.Equal(t, test.match, test.hostPlatformMatcher.Match(test.testPlatform), "should match: %t, %s to %s", test.match, test.hostPlatformMatcher.Platform, test.testPlatform)
+	}
+}
+
 func TestMatchComparerMatch_LCOW(t *testing.T) {
 	major, minor, build := windows.RtlGetNtVersionNumbers()
 	buildStr := fmt.Sprintf("%d.%d.%d", major, minor, build)
diff --git a/platforms/platforms.go b/platforms/platforms.go
index 0254ec0c5..5aee03a7e 100644
--- a/platforms/platforms.go
+++ b/platforms/platforms.go
@@ -213,6 +213,10 @@ func Parse(specifier string) (specs.Platform, error) {
 				p.Variant = cpuVariant()
 			}
 
+			if p.OS == "windows" {
+				p.OSVersion = GetWindowsOsVersion()
+			}
+
 			return p, nil
 		}
 
@@ -235,6 +239,10 @@ func Parse(specifier string) (specs.Platform, error) {
 			p.Variant = ""
 		}
 
+		if p.OS == "windows" {
+			p.OSVersion = GetWindowsOsVersion()
+		}
+
 		return p, nil
 	case 3:
 		// we have a fully specified variant, this is rare
@@ -244,6 +252,10 @@ func Parse(specifier string) (specs.Platform, error) {
 			p.Variant = "v8"
 		}
 
+		if p.OS == "windows" {
+			p.OSVersion = GetWindowsOsVersion()
+		}
+
 		return p, nil
 	}
 
diff --git a/platforms/platforms_other.go b/platforms/platforms_other.go
index 03f4dcd99..59beeb3d1 100644
--- a/platforms/platforms_other.go
+++ b/platforms/platforms_other.go
@@ -28,3 +28,7 @@ func newDefaultMatcher(platform specs.Platform) Matcher {
 		Platform: Normalize(platform),
 	}
 }
+
+func GetWindowsOsVersion() string {
+	return ""
+}
diff --git a/platforms/platforms_windows.go b/platforms/platforms_windows.go
index 950e2a2dd..733d18dde 100644
--- a/platforms/platforms_windows.go
+++ b/platforms/platforms_windows.go
@@ -17,7 +17,10 @@
 package platforms
 
 import (
+	"fmt"
+
 	specs "github.com/opencontainers/image-spec/specs-go/v1"
+	"golang.org/x/sys/windows"
 )
 
 // NewMatcher returns a Windows matcher that will match on osVersionPrefix if
@@ -32,3 +35,8 @@ func newDefaultMatcher(platform specs.Platform) Matcher {
 		},
 	}
 }
+
+func GetWindowsOsVersion() string {
+	major, minor, build := windows.RtlGetNtVersionNumbers()
+	return fmt.Sprintf("%d.%d.%d", major, minor, build)
+}