diff --git a/core/src/cli/cli.ts b/core/src/cli/cli.ts
index 03153cc34e..8ed1b82aa7 100644
--- a/core/src/cli/cli.ts
+++ b/core/src/cli/cli.ts
@@ -40,6 +40,7 @@ import { GardenPluginCallback } from "../types/plugin/plugin"
 import { renderError } from "../logger/renderers"
 import { EnterpriseApi } from "../enterprise/api"
 import chalk = require("chalk")
+import { registerSession } from "../enterprise/session-lifecycle"
 
 export async function makeDummyGarden(root: string, gardenOpts: GardenOpts) {
   const environments = gardenOpts.environmentName
@@ -282,6 +283,20 @@ ${renderCommands(commands)}
           const runningServers = await dashboardEventStream.updateTargets()
 
           if (persistent && command.server) {
+            if (enterpriseApi) {
+              // TODO: provide the environment & namespace IDs returned by this helper to `this.bufferedEventStream`,
+              // and include them in all log/event batches once the API is ready for / expects that.
+              await registerSession({
+                log,
+                enterpriseApi,
+                sessionId,
+                commandInfo,
+                localServerPort: command.server.port,
+                projectId: enterpriseApi.projectId,
+                environment: garden.environmentName,
+                namespace: garden.namespace,
+              })
+            }
             // If there is an explicit `garden dashboard` process running for the current project+env, and a server
             // is started in this Command, we show the URL to the external dashboard. Otherwise the built-in one.
             const dashboardProcess = GardenProcess.getDashboardProcess(runningServers, {
diff --git a/core/src/enterprise/session-lifecycle.ts b/core/src/enterprise/session-lifecycle.ts
new file mode 100644
index 0000000000..636ba723c3
--- /dev/null
+++ b/core/src/enterprise/session-lifecycle.ts
@@ -0,0 +1,73 @@
+/*
+ * Copyright (C) 2018-2021 Garden Technologies, Inc. <info@garden.io>
+ *
+ * This Source Code Form is subject to the terms of the Mozilla Public
+ * License, v. 2.0. If a copy of the MPL was not distributed with this
+ * file, You can obtain one at http://mozilla.org/MPL/2.0/.
+ */
+
+import { LogEntry } from "../logger/log-entry"
+import { CommandInfo } from "../plugin-context"
+import { deline } from "../util/string"
+import { EnterpriseApi, isGotError } from "./api"
+
+export interface RegisterSessionParams {
+  enterpriseApi: EnterpriseApi
+  sessionId: string
+  commandInfo: CommandInfo
+  localServerPort?: number
+  projectId: string
+  environment: string
+  namespace: string
+  log: LogEntry
+}
+
+export interface RegisterSessionResponse {
+  environmentId: number
+  namespaceId: number
+}
+
+// TODO: Read this from the `api-types` package once the session registration logic has been released in Cloud.
+/**
+ * Registers a session for a persistent command with Garden Cloud/Enterprise. This is to help the Cloud/Enterprise
+ * UI communicate with the locally running Core process.
+ */
+export async function registerSession({
+  enterpriseApi,
+  sessionId,
+  commandInfo,
+  localServerPort,
+  projectId,
+  environment,
+  namespace,
+  log,
+}: RegisterSessionParams): Promise<RegisterSessionResponse | null> {
+  try {
+    const body = {
+      sessionId,
+      commandInfo,
+      localServerPort,
+      projectUid: projectId,
+      environment,
+      namespace,
+    }
+    const res: RegisterSessionResponse = await enterpriseApi.post("sessions", {
+      body,
+      retry: true,
+      retryDescription: "Registering session",
+    })
+    return res
+  } catch (err) {
+    if (isGotError(err, 422)) {
+      const errMsg = deline`
+        Session registration failed due to mismatch between CLI and API versions. Please make sure your Garden CLI
+        version is compatible with your version of Garden Enterprise.
+      `
+      log.error(errMsg)
+    } else {
+      log.error(`An error occurred while registering the session: ${err.message}`)
+    }
+    // We don't want the command to fail when an error occurs during session registration.
+    return null
+  }
+}