diff --git a/commands/docker.go b/commands/docker.go
index 6e1b7349..2d977a2b 100644
--- a/commands/docker.go
+++ b/commands/docker.go
@@ -1,9 +1,11 @@
 package commands
 
 import (
+	"fmt"
 	"kool-dev/kool/core/builder"
 	"kool-dev/kool/core/environment"
 	"os"
+	"path"
 	"runtime"
 
 	"github.com/spf13/cobra"
@@ -15,6 +17,7 @@ type KoolDockerFlags struct {
 	Volumes      []string
 	Publish      []string
 	Network      []string
+	Context      string
 }
 
 // KoolDocker holds handlers and functions to implement the docker command logic
@@ -39,7 +42,7 @@ func AddKoolDocker(root *cobra.Command) {
 func NewKoolDocker() *KoolDocker {
 	return &KoolDocker{
 		*newDefaultKoolService(),
-		&KoolDockerFlags{[]string{}, []string{}, []string{}, []string{}},
+		&KoolDockerFlags{[]string{}, []string{}, []string{}, []string{}, ""},
 		environment.NewEnvStorage(),
 		builder.NewCommand("docker", "run", "--init", "--rm", "-w", "/app", "-i"),
 	}
@@ -49,6 +52,14 @@ func NewKoolDocker() *KoolDocker {
 func (d *KoolDocker) Execute(args []string) (err error) {
 	workDir, _ := os.Getwd()
 
+	if context := d.Flags.Context; context != "" {
+		workDir = path.Join(workDir, context)
+		if _, err = os.Stat(workDir); err != nil {
+			err = fmt.Errorf("please enter a valid context directory")
+			return
+		}
+	}
+
 	if d.Shell().IsTerminal() {
 		d.dockerRun.AppendArgs("-t")
 	}
@@ -107,6 +118,7 @@ the [COMMAND] to provide optional arguments required by the COMMAND.`,
 	cmd.Flags().StringArrayVarP(&docker.Flags.Volumes, "volume", "v", []string{}, "Bind mount a volume.")
 	cmd.Flags().StringArrayVarP(&docker.Flags.Publish, "publish", "p", []string{}, "Publish a container's port(s) to the host.")
 	cmd.Flags().StringArrayVarP(&docker.Flags.Network, "network", "n", []string{}, "Connect a container to a network.")
+	cmd.Flags().StringVarP(&docker.Flags.Context, "context", "c", "", "Working directory context.")
 
 	//After a non-flag arg, stop parsing flags
 	cmd.Flags().SetInterspersed(false)
diff --git a/commands/docker_test.go b/commands/docker_test.go
index 366c672c..75f8d0b9 100644
--- a/commands/docker_test.go
+++ b/commands/docker_test.go
@@ -7,6 +7,7 @@ import (
 	"kool-dev/kool/core/environment"
 	"kool-dev/kool/core/shell"
 	"os"
+	"path"
 	"runtime"
 	"testing"
 )
@@ -14,7 +15,7 @@ import (
 func newFakeKoolDocker() *KoolDocker {
 	return &KoolDocker{
 		*(newDefaultKoolService().Fake()),
-		&KoolDockerFlags{[]string{}, []string{}, []string{}, []string{}},
+		&KoolDockerFlags{[]string{}, []string{}, []string{}, []string{}, ""},
 		environment.NewFakeEnvStorage(),
 		&builder.FakeCommand{MockCmd: "docker"},
 	}
@@ -23,7 +24,7 @@ func newFakeKoolDocker() *KoolDocker {
 func newFailedFakeKoolDocker() *KoolDocker {
 	return &KoolDocker{
 		*(newDefaultKoolService().Fake()),
-		&KoolDockerFlags{[]string{}, []string{}, []string{}, []string{}},
+		&KoolDockerFlags{[]string{}, []string{}, []string{}, []string{}, ""},
 		environment.NewFakeEnvStorage(),
 		&builder.FakeCommand{MockCmd: "docker", MockInteractiveError: errors.New("error docker")},
 	}
@@ -50,6 +51,10 @@ func TestNewKoolDocker(t *testing.T) {
 		if len(k.Flags.Publish) > 0 {
 			t.Errorf("bad default value for Publish flag on default KoolDocker instance")
 		}
+
+		if k.Flags.Context != "" {
+			t.Errorf("bad default value for Context flag on default KoolDocker instance")
+		}
 	}
 
 	if _, ok := k.dockerRun.(*builder.DefaultCommand); !ok {
@@ -269,3 +274,35 @@ func TestNonTerminalNewDockerCommand(t *testing.T) {
 		t.Errorf("bad arguments to KoolDocker.dockerRun Command on non terminal environment")
 	}
 }
+
+func TestContextFlagNewDockerCommand(t *testing.T) {
+	f := newFakeKoolDocker()
+	f.shell.(*shell.FakeShell).MockIsTerminal = false
+	cmd := NewDockerCommand(f)
+
+	cmd.SetArgs([]string{"--context=context_test", "image"})
+
+	workDir, _ := os.Getwd()
+	workDir = path.Join(workDir, "context_test")
+	_ = os.MkdirAll(workDir, 0755)
+
+	if err := cmd.Execute(); err != nil {
+		t.Errorf("unexpected error executing docker command; error: %v", err)
+	}
+
+	argsAppend := f.dockerRun.(*builder.FakeCommand).ArgsAppend
+
+	if argsAppend[0] != "--volume" || argsAppend[1] != workDir+":/app:delegated" {
+		t.Errorf("bad arguments to KoolDocker.dockerRun Command with context flag: %v", argsAppend)
+	}
+}
+
+func TestInvalidContextFlagNewDockerCommand(t *testing.T) {
+	f := newFakeKoolDocker()
+	f.shell.(*shell.FakeShell).MockIsTerminal = false
+	cmd := NewDockerCommand(f)
+
+	cmd.SetArgs([]string{"--context=invalid_context", "image"})
+
+	assertExecGotError(t, cmd, "please enter a valid context directory")
+}
diff --git a/docs/4-Commands/kool-docker.md b/docs/4-Commands/kool-docker.md
index 716f5161..f794a07a 100644
--- a/docs/4-Commands/kool-docker.md
+++ b/docs/4-Commands/kool-docker.md
@@ -16,6 +16,7 @@ kool docker [OPTIONS] IMAGE [COMMAND] [--] [ARG...]
 ### Options
 
 ```
+  -c, --context string        Working directory context.
   -e, --env stringArray       Environment variables.
   -h, --help                  help for docker
   -n, --network stringArray   Connect a container to a network.