diff --git a/testing/internal/e2e/tests/base/target_tcp_connect_localhost_test.go b/testing/internal/e2e/tests/base/target_tcp_connect_localhost_test.go
index ea8e22134b..6928835177 100644
--- a/testing/internal/e2e/tests/base/target_tcp_connect_localhost_test.go
+++ b/testing/internal/e2e/tests/base/target_tcp_connect_localhost_test.go
@@ -16,6 +16,8 @@ import (
 	"github.com/stretchr/testify/require"
 )
 
+// TestCliTcpTargetConnectTargetWithLocalhost uses the boundary cli to connect
+// to a target using `boundary connect` and then `ssh localhost`
 func TestCliTcpTargetConnectTargetWithLocalhost(t *testing.T) {
 	e2e.MaybeSkipTest(t)
 	c, err := loadTestConfig()
diff --git a/testing/internal/e2e/tests/base/target_tcp_connect_ssh_remote_command_test.go b/testing/internal/e2e/tests/base/target_tcp_connect_ssh_remote_command_test.go
new file mode 100644
index 0000000000..d028ad15da
--- /dev/null
+++ b/testing/internal/e2e/tests/base/target_tcp_connect_ssh_remote_command_test.go
@@ -0,0 +1,84 @@
+// Copyright (c) HashiCorp, Inc.
+// SPDX-License-Identifier: BUSL-1.1
+
+package base_test
+
+import (
+	"context"
+	"encoding/json"
+	"os"
+	"strings"
+	"testing"
+
+	"github.com/hashicorp/boundary/api/targets"
+	"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"
+)
+
+// TestCliTcpTargetConnectTargetWithSshRemoteCommand uses the boundary cli to
+// connect to a target using `connect ssh -remote-commmand`
+func TestCliTcpTargetConnectTargetWithSshRemoteCommand(t *testing.T) {
+	e2e.MaybeSkipTest(t)
+	c, err := loadTestConfig()
+	require.NoError(t, err)
+
+	ctx := context.Background()
+	boundary.AuthenticateAdminCli(t, ctx)
+	newOrgId := boundary.CreateNewOrgCli(t, ctx)
+	t.Cleanup(func() {
+		ctx := context.Background()
+		boundary.AuthenticateAdminCli(t, ctx)
+		output := e2e.RunCommand(ctx, "boundary", e2e.WithArgs("scopes", "delete", "-id", newOrgId))
+		require.NoError(t, output.Err, string(output.Stderr))
+	})
+	newProjectId := boundary.CreateNewProjectCli(t, ctx, newOrgId)
+	newHostCatalogId := boundary.CreateNewHostCatalogCli(t, ctx, newProjectId)
+	newHostSetId := boundary.CreateNewHostSetCli(t, ctx, newHostCatalogId)
+	newHostId := boundary.CreateNewHostCli(t, ctx, newHostCatalogId, c.TargetIp)
+	boundary.AddHostToHostSetCli(t, ctx, newHostSetId, newHostId)
+	newTargetId := boundary.CreateNewTargetCli(t, ctx, newProjectId, c.TargetPort)
+	boundary.AddHostSourceToTargetCli(t, ctx, newTargetId, newHostSetId)
+	newCredentialStoreId := boundary.CreateNewCredentialStoreStaticCli(t, ctx, newProjectId)
+	newCredentialsId := boundary.CreateNewStaticCredentialPrivateKeyCli(t, ctx, newCredentialStoreId, c.TargetSshUser, c.TargetSshKeyPath)
+	boundary.AddBrokeredCredentialSourceToTargetCli(t, ctx, newTargetId, newCredentialsId)
+
+	// Get credentials for target
+	output := e2e.RunCommand(ctx, "boundary",
+		e2e.WithArgs("targets", "authorize-session", "-id", newTargetId, "-format", "json"),
+	)
+	require.NoError(t, output.Err, string(output.Stderr))
+	var newSessionAuthorizationResult targets.SessionAuthorizationResult
+	err = json.Unmarshal(output.Stdout, &newSessionAuthorizationResult)
+	require.NoError(t, err)
+
+	newSessionAuthorization := newSessionAuthorizationResult.Item
+	retrievedUser, ok := newSessionAuthorization.Credentials[0].Credential["username"].(string)
+	require.True(t, ok)
+	retrievedKey, ok := newSessionAuthorization.Credentials[0].Credential["private_key"].(string)
+	require.True(t, ok)
+	retrievedKey += "\n"
+	assert.Equal(t, c.TargetSshUser, retrievedUser)
+
+	k, err := os.ReadFile(c.TargetSshKeyPath)
+	require.NoError(t, err)
+	require.Equal(t, string(k), retrievedKey)
+	t.Log("Successfully retrieved credentials for target")
+
+	// Connect to target using ssh option
+	output = e2e.RunCommand(ctx, "boundary",
+		e2e.WithArgs(
+			"connect", "ssh",
+			"-target-id", newTargetId,
+			"-remote-command", "hostname -i",
+			"--",
+			"-o", "UserKnownHostsFile=/dev/null",
+			"-o", "StrictHostKeyChecking=no",
+			"-o", "IdentitiesOnly=yes", // forces the use of the provided key
+		),
+	)
+	require.NoError(t, output.Err, string(output.Stderr))
+	require.Equal(t, c.TargetIp, strings.TrimSpace(string(output.Stdout)))
+	t.Log("Successfully connected to target")
+}
diff --git a/testing/internal/e2e/tests/base/target_tcp_connect_ssh_test.go b/testing/internal/e2e/tests/base/target_tcp_connect_ssh_test.go
index 02fe8e5401..df45277642 100644
--- a/testing/internal/e2e/tests/base/target_tcp_connect_ssh_test.go
+++ b/testing/internal/e2e/tests/base/target_tcp_connect_ssh_test.go
@@ -16,9 +16,8 @@ import (
 	"github.com/stretchr/testify/require"
 )
 
-// TestCliTcpTargetConnectTargetWithSsh uses the boundary cli to create a credential using boundary's
-// built-in credential store. The test attaches that credential to a target and attempts to connect
-// to that target using those credentials.
+// TestCliTcpTargetConnectTargetWithSsh uses the boundary cli to
+// connect to a target using `connect ssh`
 func TestCliTcpTargetConnectTargetWithSsh(t *testing.T) {
 	e2e.MaybeSkipTest(t)
 	c, err := loadTestConfig()