diff --git a/.github/workflows/home-view-unit-test.yaml b/.github/workflows/home-view-unit-test.yaml
index 1e234a7f7..143ab9141 100644
--- a/.github/workflows/home-view-unit-test.yaml
+++ b/.github/workflows/home-view-unit-test.yaml
@@ -1,7 +1,7 @@
-name: Lint
+name: Unit-Test
 on: [workflow_call]
 jobs:
-  lint:
+  test:
     runs-on: ubuntu-latest
     defaults:
       run:
@@ -13,5 +13,6 @@ jobs:
           node-version: "20"
           cache: "npm"
           cache-dependency-path: "**/package-lock.json"
+      - run: npm install --prefix ../..
       - run: npm install
       - run: npm test
diff --git a/extensions/vscode/package.json b/extensions/vscode/package.json
index d9da3a397..db09cb9be 100644
--- a/extensions/vscode/package.json
+++ b/extensions/vscode/package.json
@@ -135,6 +135,11 @@
         "title": "Select Active Configuration For Deployment",
         "category": "Posit Publisher"
       },
+      {
+        "command": "posit.publisher.homeView.associateDeployment",
+        "title": "Associate with a Different Deployment on Connect",
+        "category": "Posit Publisher"
+      },
       {
         "command": "posit.publisher.homeView.createConfigForDeployment",
         "title": "Create New Configuration For Destination",
@@ -325,6 +330,10 @@
           "command": "posit.publisher.homeView.showSelectConfigForDeployment",
           "when": "webviewId == 'posit.publisher.homeView' && webviewSection == 'even-easier-deploy-more-menu-matching-configs'"
         },
+        {
+          "command": "posit.publisher.homeView.associateDeployment",
+          "when": "webviewId == 'posit.publisher.homeView' && webviewSection == 'even-easier-deploy-more-menu-matching-configs' && posit.publish.selection.hasCredentialMatch == 'true' && posit.publish.selection.isPreContentRecord == 'false'"
+        },
         {
           "command": "posit.publisher.homeView.createConfigForDeployment",
           "when": "webviewId == 'posit.publisher.homeView' && webviewSection == 'even-easier-deploy-more-menu-no-matching-configs'"
diff --git a/extensions/vscode/src/actions/showAssociateGUID.ts b/extensions/vscode/src/actions/showAssociateGUID.ts
index 7d89f9d74..73ba7164a 100644
--- a/extensions/vscode/src/actions/showAssociateGUID.ts
+++ b/extensions/vscode/src/actions/showAssociateGUID.ts
@@ -6,6 +6,7 @@ import { PublisherState } from "src/state";
 import { showProgress } from "src/utils/progress";
 import { Views } from "src/constants";
 import { useApi } from "src/api";
+import { getSummaryStringFromError } from "src/utils/errors";
 
 export async function showAssociateGUID(state: PublisherState) {
   const urlOrGuid = "";
@@ -43,13 +44,26 @@ export async function showAssociateGUID(state: PublisherState) {
     return undefined;
   }
   await showProgress("Updating Content Record", Views.HomeView, async () => {
-    const api = await useApi();
-    await api.contentRecords.patch(
-      targetContentRecord.deploymentName,
-      targetContentRecord.projectDir,
-      {
-        guid,
-      },
-    );
+    try {
+      const api = await useApi();
+      await api.contentRecords.patch(
+        targetContentRecord.deploymentName,
+        targetContentRecord.projectDir,
+        {
+          guid,
+        },
+      );
+      window.showInformationMessage(
+        `Your deployment is now locally associated with Content GUID ${guid} as requested.`,
+      );
+    } catch (error: unknown) {
+      const summary = getSummaryStringFromError(
+        "showAssociateGUID, contentRecords.patch",
+        error,
+      );
+      window.showErrorMessage(
+        `Unable to associate deployment with Content GUID ${guid}. ${summary}`,
+      );
+    }
   });
 }
diff --git a/extensions/vscode/src/constants.ts b/extensions/vscode/src/constants.ts
index e072f448c..81138b10a 100644
--- a/extensions/vscode/src/constants.ts
+++ b/extensions/vscode/src/constants.ts
@@ -66,6 +66,7 @@ const homeViewCommands = {
   Refresh: "posit.publisher.homeView.refresh",
   ShowSelectConfigForDeployment:
     "posit.publisher.homeView.showSelectConfigForDeployment",
+  AssociateDeployment: "posit.publisher.homeView.associateDeployment",
   CreateConfigForDeployment:
     "posit.publisher.homeView.createConfigForDeployment",
   SelectDeployment: "posit.publisher.homeView.selectDeployment",
diff --git a/extensions/vscode/src/extension.ts b/extensions/vscode/src/extension.ts
index 412d444a7..9e18beff3 100644
--- a/extensions/vscode/src/extension.ts
+++ b/extensions/vscode/src/extension.ts
@@ -31,6 +31,20 @@ enum InitializationInProgress {
   false = "false",
 }
 
+const SELECTION_HAS_CREDENTIAL_MATCH_CONTEXT =
+  "posit.publish.selection.hasCredentialMatch";
+export enum SelectionCredentialMatch {
+  true = "true",
+  false = "false",
+}
+
+const SELECTION_IS_PRE_CONTENT_RECORD_CONTEXT =
+  "posit.publish.selection.isPreContentRecord";
+export enum SelectionIsPreContentRecord {
+  true = "true",
+  false = "false",
+}
+
 // Once the extension is activate, hang on to the service so that we can stop it on deactivation.
 let service: Service;
 
@@ -42,6 +56,26 @@ function setInitializationInProgressContext(context: InitializationInProgress) {
   commands.executeCommand("setContext", INITIALIZING_CONTEXT, context);
 }
 
+export function setSelectionHasCredentialMatch(
+  context: SelectionCredentialMatch,
+) {
+  commands.executeCommand(
+    "setContext",
+    SELECTION_HAS_CREDENTIAL_MATCH_CONTEXT,
+    context,
+  );
+}
+
+export function setSelectionIsPreContentRecord(
+  context: SelectionIsPreContentRecord,
+) {
+  commands.executeCommand(
+    "setContext",
+    SELECTION_IS_PRE_CONTENT_RECORD_CONTEXT,
+    context,
+  );
+}
+
 // This method is called when your extension is activated
 // Your extension is activated the very first time the command is executed
 export async function activate(context: ExtensionContext) {
diff --git a/extensions/vscode/src/types/messages/webviewToHostMessages.ts b/extensions/vscode/src/types/messages/webviewToHostMessages.ts
index b83a064d5..9f830db54 100644
--- a/extensions/vscode/src/types/messages/webviewToHostMessages.ts
+++ b/extensions/vscode/src/types/messages/webviewToHostMessages.ts
@@ -27,6 +27,8 @@ export enum WebviewToHostMessageType {
   NEW_CREDENTIAL = "newCredential",
   VIEW_PUBLISHING_LOG = "viewPublishingLog",
   SHOW_ASSOCIATE_GUID = "ShowAssociateGUID",
+  UPDATE_SELECTION_CREDENTIAL_STATE = "UpdateSelectionCredentialStateMsg",
+  UPDATE_SELECTION_IS_PRE_CONTENT_RECORD = "UpdateSelectionIsPreContentRecordMsg",
 }
 
 export type AnyWebviewToHostMessage<
@@ -62,7 +64,9 @@ export type WebviewToHostMessage =
   | NewCredentialForDeploymentMsg
   | NewCredentialMsg
   | ViewPublishingLog
-  | ShowAssociateGUIDMsg;
+  | ShowAssociateGUIDMsg
+  | UpdateSelectionCredentialStateMsg
+  | UpdateSelectionIsPreContentRecordMsg;
 
 // eslint-disable-next-line @typescript-eslint/no-explicit-any
 export function isWebviewToHostMessage(msg: any): msg is WebviewToHostMessage {
@@ -89,7 +93,9 @@ export function isWebviewToHostMessage(msg: any): msg is WebviewToHostMessage {
     msg.kind === WebviewToHostMessageType.NEW_CREDENTIAL_FOR_DEPLOYMENT ||
     msg.kind === WebviewToHostMessageType.NEW_CREDENTIAL ||
     msg.kind === WebviewToHostMessageType.VIEW_PUBLISHING_LOG ||
-    msg.kind === WebviewToHostMessageType.SHOW_ASSOCIATE_GUID
+    msg.kind === WebviewToHostMessageType.SHOW_ASSOCIATE_GUID ||
+    msg.kind === WebviewToHostMessageType.UPDATE_SELECTION_CREDENTIAL_STATE ||
+    msg.kind === WebviewToHostMessageType.UPDATE_SELECTION_IS_PRE_CONTENT_RECORD
   );
 }
 
@@ -210,3 +216,17 @@ export type ViewPublishingLog =
 
 export type ShowAssociateGUIDMsg =
   AnyWebviewToHostMessage<WebviewToHostMessageType.SHOW_ASSOCIATE_GUID>;
+
+export type UpdateSelectionCredentialStateMsg = AnyWebviewToHostMessage<
+  WebviewToHostMessageType.UPDATE_SELECTION_CREDENTIAL_STATE,
+  {
+    state: string;
+  }
+>;
+
+export type UpdateSelectionIsPreContentRecordMsg = AnyWebviewToHostMessage<
+  WebviewToHostMessageType.UPDATE_SELECTION_IS_PRE_CONTENT_RECORD,
+  {
+    state: string;
+  }
+>;
diff --git a/extensions/vscode/src/views/homeView.ts b/extensions/vscode/src/views/homeView.ts
index ec52885f7..9d2762085 100644
--- a/extensions/vscode/src/views/homeView.ts
+++ b/extensions/vscode/src/views/homeView.ts
@@ -82,6 +82,12 @@ import { showAssociateGUID } from "src/actions/showAssociateGUID";
 import { extensionSettings } from "src/extension";
 import { openFileInEditor } from "src/commands";
 import { showImmediateDeploymentFailureMessage } from "./publishFailures";
+import {
+  SelectionCredentialMatch,
+  setSelectionHasCredentialMatch,
+  SelectionIsPreContentRecord,
+  setSelectionIsPreContentRecord,
+} from "../extension";
 
 enum HomeViewInitialized {
   initialized = "initialized",
@@ -174,6 +180,10 @@ export class HomeViewProvider implements WebviewViewProvider, Disposable {
         return this.showPublishingLog();
       case WebviewToHostMessageType.SHOW_ASSOCIATE_GUID:
         return showAssociateGUID(this.state);
+      case WebviewToHostMessageType.UPDATE_SELECTION_CREDENTIAL_STATE:
+        return this.updateSelectionCredentialState(msg.content.state);
+      case WebviewToHostMessageType.UPDATE_SELECTION_IS_PRE_CONTENT_RECORD:
+        return this.updateSelectionIsPreContentRecordState(msg.content.state);
       default:
         window.showErrorMessage(
           `Internal Error: onConduitMessage unhandled msg: ${JSON.stringify(msg)}`,
@@ -189,6 +199,22 @@ export class HomeViewProvider implements WebviewViewProvider, Disposable {
     );
   }
 
+  private async updateSelectionCredentialState(state: string) {
+    const match =
+      state === SelectionCredentialMatch.true
+        ? SelectionCredentialMatch.true
+        : SelectionCredentialMatch.false;
+    return await setSelectionHasCredentialMatch(match);
+  }
+
+  private async updateSelectionIsPreContentRecordState(state: string) {
+    const match =
+      state === SelectionIsPreContentRecord.true
+        ? SelectionIsPreContentRecord.true
+        : SelectionIsPreContentRecord.false;
+    return await setSelectionIsPreContentRecord(match);
+  }
+
   private async initiateDeployment(
     deploymentName: string,
     credentialName: string,
@@ -1782,6 +1808,11 @@ export class HomeViewProvider implements WebviewViewProvider, Disposable {
         this.showSelectOrCreateConfigForDeployment,
         this,
       ),
+      commands.registerCommand(
+        Commands.HomeView.AssociateDeployment,
+        () => showAssociateGUID(this.state),
+        this,
+      ),
       commands.registerCommand(
         Commands.HomeView.CreateConfigForDeployment,
         this.showSelectOrCreateConfigForDeployment,
diff --git a/extensions/vscode/webviews/homeView/src/stores/home.ts b/extensions/vscode/webviews/homeView/src/stores/home.ts
index 8ed986e0b..68c88b6b7 100644
--- a/extensions/vscode/webviews/homeView/src/stores/home.ts
+++ b/extensions/vscode/webviews/homeView/src/stores/home.ts
@@ -9,6 +9,7 @@ import {
   PreContentRecord,
   Configuration,
   ConfigurationError,
+  isPreContentRecord,
 } from "../../../../src/api";
 import { isConfigurationError } from "../../../../src/api/types/configurations";
 import { WebviewToHostMessageType } from "../../../../src/types/messages/webviewToHostMessages";
@@ -179,6 +180,34 @@ export const useHomeStore = defineStore("home", () => {
     selectedContentRecord.value = contentRecord;
   }
 
+  watch([serverCredential], () => updateSelectionCredentialStatus());
+
+  const updateSelectionCredentialStatus = () => {
+    const hostConduit = useHostConduitService();
+    hostConduit.sendMsg({
+      kind: WebviewToHostMessageType.UPDATE_SELECTION_CREDENTIAL_STATE,
+      content: {
+        state: serverCredential.value !== undefined ? "true" : "false",
+      },
+    });
+  };
+
+  watch([selectedContentRecord], () =>
+    updateSelectionIsPreContentRecordState(),
+  );
+
+  const updateSelectionIsPreContentRecordState = () => {
+    const hostConduit = useHostConduitService();
+    hostConduit.sendMsg({
+      kind: WebviewToHostMessageType.UPDATE_SELECTION_IS_PRE_CONTENT_RECORD,
+      content: {
+        state: isPreContentRecord(selectedContentRecord.value)
+          ? "true"
+          : "false",
+      },
+    });
+  };
+
   watch([selectedConfiguration], () => updateParentViewSelectionState());
 
   const updateParentViewSelectionState = () => {