diff --git a/changes/38785-windows-setup-experience-cancel b/changes/38785-windows-setup-experience-cancel
new file mode 100644
index 0000000000..7fffb77759
--- /dev/null
+++ b/changes/38785-windows-setup-experience-cancel
@@ -0,0 +1 @@
+- Added `require_all_software_windows` setting to cancel the Windows setup experience if any software install fails during Autopilot enrollment, matching the existing macOS behavior.
diff --git a/server/service/setup_experience.go b/server/service/setup_experience.go
index cd26b8b717..00203aa7cd 100644
--- a/server/service/setup_experience.go
+++ b/server/service/setup_experience.go
@@ -238,22 +238,31 @@ func (svc *Service) IsAllSetupExperienceSoftwareRequired(ctx context.Context, ho
 }
 
 func isAllSetupExperienceSoftwareRequired(ctx context.Context, ds fleet.Datastore, host *fleet.Host) (bool, error) {
+	// Only macOS and Windows support canceling setup if software fails.
+	if host.Platform != "darwin" && host.Platform != "windows" {
+		return false, nil
+	}
+
 	teamID := host.TeamID
-	requireAllSoftware := false
 	if teamID == nil || *teamID == 0 {
 		ac, err := ds.AppConfig(ctx)
 		if err != nil {
 			return false, ctxerr.Wrap(ctx, err, "getting app config")
 		}
-		requireAllSoftware = ac.MDM.MacOSSetup.RequireAllSoftware
-	} else {
-		team, err := ds.TeamLite(ctx, *teamID)
-		if err != nil {
-			return false, ctxerr.Wrap(ctx, err, "load team")
+		if host.Platform == "windows" {
+			return ac.MDM.MacOSSetup.RequireAllSoftwareWindows, nil
 		}
-		requireAllSoftware = team.Config.MDM.MacOSSetup.RequireAllSoftware
+		return ac.MDM.MacOSSetup.RequireAllSoftware, nil
 	}
-	return requireAllSoftware, nil
+
+	team, err := ds.TeamLite(ctx, *teamID)
+	if err != nil {
+		return false, ctxerr.Wrap(ctx, err, "load team")
+	}
+	if host.Platform == "windows" {
+		return team.Config.MDM.MacOSSetup.RequireAllSoftwareWindows, nil
+	}
+	return team.Config.MDM.MacOSSetup.RequireAllSoftware, nil
 }
 
 func (svc *Service) MaybeCancelPendingSetupExperienceSteps(ctx context.Context, host *fleet.Host) error {
@@ -261,8 +270,8 @@ func (svc *Service) MaybeCancelPendingSetupExperienceSteps(ctx context.Context,
 }
 
 func maybeCancelPendingSetupExperienceSteps(ctx context.Context, ds fleet.Datastore, host *fleet.Host, newActivityFn fleet.NewActivityFunc) error {
-	// If the host is not MacOS, we do nothing.
-	if host.Platform != "darwin" {
+	// Only macOS and Windows support canceling setup experience steps.
+	if host.Platform != "darwin" && host.Platform != "windows" {
 		return nil
 	}
 
diff --git a/server/service/setup_experience_test.go b/server/service/setup_experience_test.go
index c3d3daf828..4fd449063e 100644
--- a/server/service/setup_experience_test.go
+++ b/server/service/setup_experience_test.go
@@ -221,6 +221,79 @@ func TestSetupExperienceAuth(t *testing.T) {
 	}
 }
 
+func TestIsAllSetupExperienceSoftwareRequired(t *testing.T) {
+	ds := new(mock.Store)
+
+	teamID := uint(1)
+	// Use different values for macOS vs Windows to ensure the correct field is read for each platform.
+	appCfg := &fleet.AppConfig{}
+	appCfg.MDM.MacOSSetup.RequireAllSoftware = true
+	appCfg.MDM.MacOSSetup.RequireAllSoftwareWindows = false
+
+	ds.AppConfigFunc = func(ctx context.Context) (*fleet.AppConfig, error) {
+		return appCfg, nil
+	}
+	ds.TeamLiteFunc = func(ctx context.Context, tid uint) (*fleet.TeamLite, error) {
+		return &fleet.TeamLite{
+			ID:   tid,
+			Name: "team",
+			Config: fleet.TeamConfigLite{
+				MDM: fleet.TeamMDM{
+					MacOSSetup: fleet.MacOSSetup{
+						RequireAllSoftware:        false,
+						RequireAllSoftwareWindows: true,
+					},
+				},
+			},
+		}, nil
+	}
+
+	tests := []struct {
+		name     string
+		host     *fleet.Host
+		expected bool
+	}{
+		{
+			name:     "macOS host, no team, reads macOS global config (true)",
+			host:     &fleet.Host{Platform: "darwin"},
+			expected: true,
+		},
+		{
+			name:     "macOS host, with team, reads macOS team config (false)",
+			host:     &fleet.Host{Platform: "darwin", TeamID: &teamID},
+			expected: false,
+		},
+		{
+			name:     "windows host, no team, reads Windows global config (false)",
+			host:     &fleet.Host{Platform: "windows"},
+			expected: false,
+		},
+		{
+			name:     "windows host, with team, reads Windows team config (true)",
+			host:     &fleet.Host{Platform: "windows", TeamID: &teamID},
+			expected: true,
+		},
+		{
+			name:     "linux host returns false",
+			host:     &fleet.Host{Platform: "ubuntu"},
+			expected: false,
+		},
+		{
+			name:     "ios host returns false",
+			host:     &fleet.Host{Platform: "ios"},
+			expected: false,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			result, err := isAllSetupExperienceSoftwareRequired(t.Context(), ds, tt.host)
+			require.NoError(t, err)
+			require.Equal(t, tt.expected, result)
+		})
+	}
+}
+
 func TestMaybeUpdateSetupExperience(t *testing.T) {
 	ds := new(mock.Store)
 	// _, ctx := newTestService(t, ds, nil, nil, nil)