diff --git a/testing/internal/e2e/helpers.go b/testing/internal/e2e/helpers.go
index c6ea753acb..64a4c5db2a 100644
--- a/testing/internal/e2e/helpers.go
+++ b/testing/internal/e2e/helpers.go
@@ -2,6 +2,7 @@ package e2e
 
 import (
 	"bytes"
+	"context"
 	"errors"
 	"fmt"
 	"os"
@@ -74,6 +75,30 @@ func RunCommand(name string, args ...string) *CommandResult {
 	}
 }
 
+// RunCommandContext is similar to RunCommand but allows passing in a context
+func RunCommandContext(ctx context.Context, name string, args ...string) *CommandResult {
+	var outbuf, errbuf bytes.Buffer
+
+	cmd := exec.CommandContext(ctx, name, args...)
+	cmd.Stdout = &outbuf
+	cmd.Stderr = &errbuf
+
+	err := cmd.Run()
+
+	var ee *exec.ExitError
+	var exitCode int
+	if errors.As(err, &ee) {
+		exitCode = ee.ExitCode()
+	}
+
+	return &CommandResult{
+		Stdout:   outbuf.Bytes(),
+		Stderr:   errbuf.Bytes(),
+		ExitCode: exitCode,
+		Err:      err,
+	}
+}
+
 // WithArgs is an option to RunCommand that allows the user to specify arguments
 // for the provided command
 func WithArgs(args ...string) Option {
diff --git a/testing/internal/e2e/host/static/session_test.go b/testing/internal/e2e/host/static/session_test.go
new file mode 100644
index 0000000000..ca775a8368
--- /dev/null
+++ b/testing/internal/e2e/host/static/session_test.go
@@ -0,0 +1,113 @@
+package static_test
+
+import (
+	"context"
+	"encoding/json"
+	"errors"
+	"testing"
+	"time"
+
+	"github.com/cenkalti/backoff/v4"
+	"github.com/hashicorp/boundary/api/sessions"
+	"github.com/hashicorp/boundary/testing/internal/e2e"
+	"github.com/hashicorp/boundary/testing/internal/e2e/boundary"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+)
+
+func TestSessionCancelingCli(t *testing.T) {
+	e2e.MaybeSkipTest(t)
+	c, err := loadConfig()
+	require.NoError(t, err)
+
+	boundary.AuthenticateCli(t)
+	newOrgId := boundary.CreateNewOrgCli(t)
+	newProjectId := boundary.CreateNewProjectCli(t, newOrgId)
+	newHostCatalogId := boundary.CreateNewHostCatalogCli(t, newProjectId)
+	newHostSetId := boundary.CreateNewHostSetCli(t, newHostCatalogId)
+	newHostId := boundary.CreateNewHostCli(t, newHostCatalogId, c.TargetIp)
+	boundary.AddHostToHostSetCli(t, newHostSetId, newHostId)
+	newTargetId := boundary.CreateNewTargetCli(t, newProjectId, c.TargetPort)
+	boundary.AddHostSourceToTargetCli(t, newTargetId, newHostSetId)
+
+	// Connect to target to create a session
+	ctx, cancel := context.WithCancel(context.Background())
+	errChan := make(chan *e2e.CommandResult)
+	go func() {
+		errChan <- e2e.RunCommandContext(ctx, "boundary", "connect",
+			"-target-id", newTargetId,
+			"-exec", "/usr/bin/ssh", "--",
+			"-l", c.TargetSshUser,
+			"-i", c.TargetSshKeyPath,
+			"-o", "UserKnownHostsFile=/dev/null",
+			"-o", "StrictHostKeyChecking=no",
+			"-o", "IdentitiesOnly=yes", // forces the use of the provided key
+			"-p", "{{boundary.port}}", // this is provided by boundary
+			"{{boundary.ip}}",
+			"hostname -i; sleep 60",
+		)
+	}()
+	t.Cleanup(cancel)
+
+	// Get list of sessions
+	var session *sessions.Session
+	err = backoff.RetryNotify(
+		func() error {
+			output := e2e.RunCommand("boundary", "sessions", "list", "-scope-id", newProjectId, "-format", "json")
+			if output.Err != nil {
+				return backoff.Permanent(errors.New(string(output.Stderr)))
+			}
+
+			var sessionListResult sessions.SessionListResult
+			err = json.Unmarshal(output.Stdout, &sessionListResult)
+			if err != nil {
+				return backoff.Permanent(err)
+			}
+
+			sessionCount := len(sessionListResult.Items)
+			if sessionCount == 0 {
+				return errors.New("No items are appearing in the session list")
+			}
+
+			t.Logf("Found %d session(s)", sessionCount)
+			if sessionCount != 1 {
+				return backoff.Permanent(errors.New("Only one session was expected to be found"))
+			}
+
+			session = sessionListResult.Items[0]
+			return nil
+		},
+		backoff.WithMaxRetries(backoff.NewConstantBackOff(3*time.Second), 5),
+		func(err error, td time.Duration) {
+			t.Logf("%s. Retrying...", err.Error())
+		},
+	)
+	require.NoError(t, err)
+	assert.Equal(t, newTargetId, session.TargetId)
+	assert.Equal(t, newHostId, session.HostId)
+	require.Equal(t, "active", session.Status)
+
+	// Cancel session
+	output := e2e.RunCommand("boundary", "sessions", "cancel", "-id", session.Id)
+	require.NoError(t, output.Err, string(output.Stderr))
+
+	output = e2e.RunCommand("boundary", "sessions", "read", "-id", session.Id, "-format", "json")
+	require.NoError(t, output.Err, string(output.Stderr))
+	var newSessionReadResult sessions.SessionReadResult
+	err = json.Unmarshal(output.Stdout, &newSessionReadResult)
+	require.NoError(t, err)
+	require.Condition(t, func() bool {
+		return newSessionReadResult.Item.Status == "canceling" || newSessionReadResult.Item.Status == "terminated"
+	})
+
+	// Check output from session
+	select {
+	case output := <-errChan:
+		// `boundary connect` returns a 255 when cancelled
+		require.Equal(t, output.ExitCode, 255, string(output.Stdout), string(output.Stderr))
+	case <-time.After(time.Second * 5):
+		t.Fatal("Timed out waiting for session command to exit")
+	}
+
+	t.Log("Successfully cancelled session")
+}