diff --git a/CHANGELOG.md b/CHANGELOG.md
index 086ea1d0..4600e7c4 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,12 @@
 
 ## Unreleased
 
+- Previously, if a workspace stopped or restarted causing the "Start" dialog to
+  appear in VS Code, the start button would fire a start workspace request regardless
+  of the workspace status.
+  Now we perform a check to see if the workspace is still stopped or failed. If its status
+  has changed out from under the IDE, it will not fire a redundant start request.
+
 ### Changed
 
 - Previously, the extension would always log SSH proxy diagnostics to a fixed
diff --git a/CONTRIBUTING.md b/CONTRIBUTING.md
index 8671c76c..7ec93dc5 100644
--- a/CONTRIBUTING.md
+++ b/CONTRIBUTING.md
@@ -93,6 +93,11 @@ was but for now it means some things are difficult to test as you cannot import
 
 ## Development
 
+> [!IMPORTANT]
+> Reasoning about networking gets really wonky trying to develop
+> this extension from a coder workspace. We currently recommend cloning the
+> repo locally
+
 1. Run `yarn watch` in the background.
 2. OPTIONAL: Compile the `coder` binary and place it in the equivalent of
    `os.tmpdir() + "/coder"`. If this is missing, it will download the binary
diff --git a/src/api.ts b/src/api.ts
index a237a830..5a2d4c4d 100644
--- a/src/api.ts
+++ b/src/api.ts
@@ -94,7 +94,7 @@ export async function makeCoderSdk(baseUrl: string, token: string | undefined, s
 /**
  * Start or update a workspace and return the updated workspace.
  */
-export async function startWorkspace(restClient: Api, workspace: Workspace): Promise<Workspace> {
+export async function startWorkspaceIfStoppedOrFailed(restClient: Api, workspace: Workspace): Promise<Workspace> {
   // If the workspace requires the latest active template version, we should attempt
   // to update that here.
   // TODO: If param set changes, what do we do??
@@ -103,9 +103,18 @@ export async function startWorkspace(restClient: Api, workspace: Workspace): Pro
       workspace.template_active_version_id
     : // Default to not updating the workspace if not required.
       workspace.latest_build.template_version_id
-  const latestBuild = await restClient.startWorkspace(workspace.id, versionID)
+
+  // Before we start a workspace, we make an initial request to check it's not already started
+  const updatedWorkspace = await restClient.getWorkspace(workspace.id)
+
+  if (!["stopped", "failed"].includes(updatedWorkspace.latest_build.status)) {
+    return updatedWorkspace
+  }
+
+  const latestBuild = await restClient.startWorkspace(updatedWorkspace.id, versionID)
+
   return {
-    ...workspace,
+    ...updatedWorkspace,
     latest_build: latestBuild,
   }
 }
diff --git a/src/remote.ts b/src/remote.ts
index 07fb94bb..1d10c90d 100644
--- a/src/remote.ts
+++ b/src/remote.ts
@@ -10,7 +10,7 @@ import * as path from "path"
 import prettyBytes from "pretty-bytes"
 import * as semver from "semver"
 import * as vscode from "vscode"
-import { makeCoderSdk, startWorkspace, waitForBuild } from "./api"
+import { makeCoderSdk, startWorkspaceIfStoppedOrFailed, waitForBuild } from "./api"
 import { extractAgents } from "./api-helper"
 import * as cli from "./cliManager"
 import { Commands } from "./commands"
@@ -105,7 +105,7 @@ export class Remote {
                   return undefined
                 }
                 this.storage.writeToCoderOutputChannel(`Starting ${workspaceName}...`)
-                workspace = await startWorkspace(restClient, workspace)
+                workspace = await startWorkspaceIfStoppedOrFailed(restClient, workspace)
                 break
               case "failed":
                 // On a first attempt, we will try starting a failed workspace
@@ -115,7 +115,7 @@ export class Remote {
                     return undefined
                   }
                   this.storage.writeToCoderOutputChannel(`Starting ${workspaceName}...`)
-                  workspace = await startWorkspace(restClient, workspace)
+                  workspace = await startWorkspaceIfStoppedOrFailed(restClient, workspace)
                   break
                 }
               // Otherwise fall through and error.