diff --git a/templates/templates.go b/templates/templates.go
index bfc5b596..ab0f1040 100644
--- a/templates/templates.go
+++ b/templates/templates.go
@@ -20,8 +20,8 @@ type TemplateType string
 const (
 	// Snippet will mark a template as a part of a file.
 	Snippet TemplateType = "snippet"
-	// Fragment will mark a template that includes header and footer as a part of a file.
-	Fragment TemplateType = "fragment"
+	// Line is a template for a single line in a file.
+	Line TemplateType = "line"
 	// File will mark a templates as a full file.
 	File TemplateType = "file"
 	// Directory will mark a template as a directory.
@@ -120,8 +120,8 @@ func (t *Template) Validate() error {
 		return nil
 	case t.Name == "":
 		return errors.New("template name cannot be empty")
-	case t.Type != Snippet && t.Type != File && t.Type != Directory && t.Type != Fragment:
-		return errors.Errorf("invalid template type %s, it must be %s, %s, %s, or %s", t.Type, Snippet, Fragment, File, Directory)
+	case t.Type != Snippet && t.Type != File && t.Type != Directory && t.Type != Line:
+		return errors.Errorf("invalid template type %s, it must be %s, %s, %s, or %s", t.Type, Snippet, Line, File, Directory)
 	case t.TemplatePath == "" && t.Type != Directory && len(t.Content) == 0:
 		return errors.New("template template cannot be empty")
 	case t.TemplatePath != "" && t.Type == Directory:
@@ -264,9 +264,8 @@ func (o *Output) Write() error {
 		return fileutil.WriteFile(path, o.Content, 0600)
 	case Snippet:
 		return fileutil.WriteSnippet(path, o.Content, 0600)
-	case Fragment:
-		lines := strings.Split(string(o.Content), "\n")
-		return fileutil.WriteFragment(path, o.Content, lines[0], lines[len(lines)-1], 0600)
+	case Line:
+		return fileutil.WriteLine(path, o.Content, 0600)
 	default:
 		return errors.Errorf("unexpected output template type %s", string(o.Type))
 	}
diff --git a/templates/values.go b/templates/values.go
index 3749f9f0..60c0ad8f 100644
--- a/templates/values.go
+++ b/templates/values.go
@@ -21,11 +21,18 @@ type StepSSH struct {
 // Relative paths are relative to the StepPath.
 var DefaultSSHTemplates = SSHTemplates{
 	User: []Template{
+		{
+			Name:         "base_config.tpl",
+			Type:         Snippet,
+			TemplatePath: "templates/ssh/base_config.tpl",
+			Path:         "~/.ssh/config",
+			Comment:      "#",
+		},
 		{
 			Name:         "include.tpl",
-			Type:         Fragment,
+			Type:         Line,
 			TemplatePath: "templates/ssh/include.tpl",
-			Path:         "~/.ssh/config",
+			Path:         "~/.ssh/include",
 			Comment:      "#",
 		},
 		{
@@ -64,18 +71,28 @@ var DefaultSSHTemplates = SSHTemplates{
 
 // DefaultSSHTemplateData contains the data of the default templates used on ssh.
 var DefaultSSHTemplateData = map[string]string{
-	// include.tpl adds the step ssh config file.
+	// base_config.tpl adds the step ssh config file.
 	//
 	// Note: on windows `Include C:\...` is treated as a relative path.
-	"include.tpl": `{{- if .User.Authority }}# {{ .User.Authority }}
-{{ end }}# autogenerated by step
-# @ {{ now }}
-Host *
+	"base_config.tpl": `Host *
 {{- if or .User.GOOS "none" | eq "windows" }}
+{{- if .User.Authority }}
+	Include "{{ .User.Home | replace "\\" "/" | trimPrefix "C:" }}/.ssh/include"
+{{- else }}
 	Include "{{ .User.StepPath | replace "\\" "/" | trimPrefix "C:" }}/ssh/config"
+{{- end }}
+{{- else }}
+{{- if .User.Authority }}
+	Include "{{.User.Home}}/.ssh/include"
 {{- else }}
 	Include "{{.User.StepPath}}/ssh/config"
-{{ end }}# end`,
+{{- end }}
+{{- end }}`,
+
+	// include.tpl adds the step ssh config file.
+	//
+	// Note: on windows `Include C:\...` is treated as a relative path.
+	"include.tpl": `{{- if or .User.GOOS "none" | eq "windows" }}Include "{{ .User.StepPath | replace "\\" "/" | trimPrefix "C:" }}/ssh/config"{{- else }}Include "{{.User.StepPath}}/ssh/config"{{- end }}`,
 
 	// config.tpl is the step ssh config file, it includes the Match rule and
 	// references the step known_hosts file.
@@ -87,10 +104,10 @@ Host *
 {{- end }}
 {{- if or .User.GOOS "none" | eq "windows" }}
 	UserKnownHostsFile "{{.User.StepPath}}\ssh\known_hosts"
-	ProxyCommand C:\Windows\System32\cmd.exe /c step ssh proxycommand %r %h %p
+	ProxyCommand C:\Windows\System32\cmd.exe /c step ssh proxycommand{{- if .User.Context }} --context {{ .User.Context }}{{- end }} %r %h %p
 {{- else }}
 	UserKnownHostsFile "{{.User.StepPath}}/ssh/known_hosts"
-	ProxyCommand step ssh proxycommand %r %h %p
+	ProxyCommand step ssh proxycommand{{- if .User.Context }} --context {{ .User.Context }}{{- end }} %r %h %p
 {{- end }}
 `,