diff --git a/docs/docs/20-usage/20-workflow-syntax.md b/docs/docs/20-usage/20-workflow-syntax.md
index a3d04da372..3b31893f6e 100644
--- a/docs/docs/20-usage/20-workflow-syntax.md
+++ b/docs/docs/20-usage/20-workflow-syntax.md
@@ -546,7 +546,8 @@ The workspace can be customized using the workspace block in the YAML file:
 ```
 
 :::note
-Plugins will always have the workspace base at `/woodpecker`
+Plugins will always have the workspace base at `/woodpecker`.
+If windows is detected as container host os, it's `c:\woodpecker`.
 :::
 
 The base attribute defines a shared base volume available to all steps. This ensures your source code, dependencies and compiled binaries are persisted and shared between steps.
diff --git a/pipeline/frontend/yaml/compiler/compiler_test.go b/pipeline/frontend/yaml/compiler/compiler_test.go
index dadbcd5dd0..875c4c8050 100644
--- a/pipeline/frontend/yaml/compiler/compiler_test.go
+++ b/pipeline/frontend/yaml/compiler/compiler_test.go
@@ -299,6 +299,51 @@ func TestCompilerCompile(t *testing.T) {
 			backConf:    nil,
 			expectedErr: "step 'dummy' depends on unknown step 'not exist'",
 		},
+		{
+			name: "workflow that targets windows as container host",
+			fronConf: &yaml_types.Workflow{
+				Steps: yaml_types.ContainerList{ContainerList: []*yaml_types.Container{{
+					Name:     "hello powershell",
+					Image:    "mcr.microsoft.com/windows/servercore:ltsc2022",
+					Commands: []string{"powershell.exe /c 'echo hello'"},
+				}}},
+				Workspace: yaml_types.Workspace{
+					Base: "c:\\tmp",
+				},
+			},
+			backConf: &backend_types.Config{
+				Stages: []*backend_types.Stage{
+					{
+						Steps: []*backend_types.Step{{
+							Name:          "clone",
+							Type:          backend_types.StepTypeClone,
+							Image:         constant.DefaultClonePlugin,
+							OnSuccess:     true,
+							Failure:       "fail",
+							Volumes:       []string{"test_default:c:\\woodpecker"},
+							WorkingDir:    "c:\\woodpecker/src/github.com/octocat/hello-world",
+							WorkspaceBase: `c:\woodpecker`,
+							Networks:      []backend_types.Conn{{Name: "test_default", Aliases: []string{"clone"}}},
+							ExtraHosts:    []backend_types.HostAlias{},
+						}},
+					}, {Steps: []*backend_types.Step{{
+						Name:          "hello powershell",
+						Type:          backend_types.StepTypeCommands,
+						Image:         "mcr.microsoft.com/windows/servercore:ltsc2022",
+						Commands:      []string{"powershell.exe /c 'echo hello'"},
+						OnSuccess:     true,
+						Failure:       "fail",
+						Volumes:       []string{"test_default:c:\\tmp"},
+						WorkingDir:    "c:\\tmp/src/github.com/octocat/hello-world",
+						WorkspaceBase: `c:\tmp`,
+						Networks:      []backend_types.Conn{{Name: "test_default", Aliases: []string{"hello powershell"}}},
+						ExtraHosts:    []backend_types.HostAlias{},
+					}}},
+				},
+				Networks: defaultNetworks,
+				Volumes:  defaultVolumes,
+			},
+		},
 	}
 
 	for _, test := range tests {
diff --git a/pipeline/frontend/yaml/compiler/convert.go b/pipeline/frontend/yaml/compiler/convert.go
index b31747aa18..66073f4dd0 100644
--- a/pipeline/frontend/yaml/compiler/convert.go
+++ b/pipeline/frontend/yaml/compiler/convert.go
@@ -18,6 +18,7 @@ import (
 	"fmt"
 	"maps"
 	"path"
+	"regexp"
 	"strconv"
 	"strings"
 
@@ -33,10 +34,28 @@ import (
 const (
 	// The pluginWorkspaceBase should not be changed, only if you are sure what you do.
 	pluginWorkspaceBase = "/woodpecker"
+	// The pluginWorkspaceBaseWindows is like pluginWorkspaceBase but used if we detect windows as container host target.
+	pluginWorkspaceBaseWindows = `c:\woodpecker`
 	// DefaultWorkspaceBase is set if not altered by the user.
 	DefaultWorkspaceBase = pluginWorkspaceBase
 )
 
+var workspaceHasWindowsPattern = regexp.MustCompile(`^[a-zA-Z]:\\`)
+
+func (c *Compiler) checkRunOnWindowsHeuristics() bool {
+	// if user customized the workspace witch indicates it targets windows
+	if workspaceHasWindowsPattern.MatchString(c.workspaceBase) {
+		return true
+	}
+
+	// if the platform filter targets windows
+	if strings.HasPrefix(strings.ToLower(c.metadata.Sys.Platform), "windows") {
+		return true
+	}
+
+	return false
+}
+
 func (c *Compiler) createProcess(container *yaml_types.Container, stepType backend_types.StepType) (*backend_types.Step, error) {
 	var (
 		uuid = ulid.Make()
@@ -51,7 +70,11 @@ func (c *Compiler) createProcess(container *yaml_types.Container, stepType backe
 	workspaceBase := c.workspaceBase
 	if container.IsPlugin() {
 		// plugins have a predefined workspace base to not tamper with entrypoint executables
-		workspaceBase = pluginWorkspaceBase
+		if c.checkRunOnWindowsHeuristics() {
+			workspaceBase = pluginWorkspaceBaseWindows
+		} else {
+			workspaceBase = pluginWorkspaceBase
+		}
 	}
 	workspaceVolume := fmt.Sprintf("%s_default:%s", c.prefix, workspaceBase)
 
@@ -206,7 +229,12 @@ func (c *Compiler) stepWorkingDir(container *yaml_types.Container) string {
 	}
 	base := c.workspaceBase
 	if container.IsPlugin() {
-		base = pluginWorkspaceBase
+		// plugins have a predefined workspace base to not tamper with entrypoint executables
+		if c.checkRunOnWindowsHeuristics() {
+			base = pluginWorkspaceBaseWindows
+		} else {
+			base = pluginWorkspaceBase
+		}
 	}
 	return path.Join(base, c.workspacePath, container.Directory)
 }