diff --git a/frontend/pages/SoftwarePage/components/AppStoreVpp/AppStoreVpp.tsx b/frontend/pages/SoftwarePage/components/AppStoreVpp/AppStoreVpp.tsx
index 358c09ffad..1a1fc02ad0 100644
--- a/frontend/pages/SoftwarePage/components/AppStoreVpp/AppStoreVpp.tsx
+++ b/frontend/pages/SoftwarePage/components/AppStoreVpp/AppStoreVpp.tsx
@@ -20,6 +20,7 @@ import { NotificationContext } from "context/notification";
 import { getErrorReason } from "interfaces/errors";
 import { buildQueryStringFromParams } from "utilities/url";
 import SoftwareIcon from "../icons/SoftwareIcon";
+import { getErrorMessage } from "./helpers";
 
 const baseClass = "app-store-vpp";
 
@@ -171,13 +172,7 @@ const AppStoreVpp = ({ teamId, router, onExit }: IAppStoreVppProps) => {
       });
       router.push(`${PATHS.SOFTWARE}?${queryParams}`);
     } catch (e) {
-      const reason = getErrorReason(e);
-      // TODO: update with pre-defined error messages we want to pass through from the API
-      if (reason.toLowerCase().includes("already")) {
-        renderFlash("error", reason);
-      } else {
-        renderFlash("error", "Couldn’t add software. Please try again.");
-      }
+      renderFlash("error", getErrorMessage(e));
     }
     onExit();
   };
diff --git a/frontend/pages/SoftwarePage/components/AppStoreVpp/helpers.tsx b/frontend/pages/SoftwarePage/components/AppStoreVpp/helpers.tsx
new file mode 100644
index 0000000000..b32495cbb8
--- /dev/null
+++ b/frontend/pages/SoftwarePage/components/AppStoreVpp/helpers.tsx
@@ -0,0 +1,32 @@
+import React from "react";
+import { getErrorReason } from "interfaces/errors";
+
+const ADD_SOFTWARE_ERROR_PREFIX = "Couldn’t add software.";
+const DEFAULT_ERROR_MESSAGE = `${ADD_SOFTWARE_ERROR_PREFIX} Please try again.`;
+
+const generateAlreadyAvailableMessage = (msg: string) => {
+  const regex = new RegExp(
+    `${ADD_SOFTWARE_ERROR_PREFIX} (.+) already.+on the (.+) team.`
+  );
+
+  const match = msg.match(regex);
+  if (!match) return DEFAULT_ERROR_MESSAGE;
+
+  return (
+    <>
+      {ADD_SOFTWARE_ERROR_PREFIX} <b>{match[1]}</b> already has software
+      available for install on the <b>{match[2]}</b> team.{" "}
+    </>
+  );
+};
+
+// eslint-disable-next-line import/prefer-default-export
+export const getErrorMessage = (e: unknown) => {
+  const reason = getErrorReason(e);
+
+  // software is already available for install
+  if (reason.toLowerCase().includes("already")) {
+    return generateAlreadyAvailableMessage(reason);
+  }
+  return DEFAULT_ERROR_MESSAGE;
+};
diff --git a/frontend/pages/hosts/details/cards/Software/HostSoftware.tsx b/frontend/pages/hosts/details/cards/Software/HostSoftware.tsx
index 6cf80111ac..f4a369cdb4 100644
--- a/frontend/pages/hosts/details/cards/Software/HostSoftware.tsx
+++ b/frontend/pages/hosts/details/cards/Software/HostSoftware.tsx
@@ -27,6 +27,7 @@ import CustomLink from "components/CustomLink";
 import { generateSoftwareTableHeaders as generateHostSoftwareTableConfig } from "./HostSoftwareTableConfig";
 import { generateSoftwareTableHeaders as generateDeviceSoftwareTableConfig } from "./DeviceSoftwareTableConfig";
 import HostSoftwareTable from "./HostSoftwareTable";
+import { getErrorMessage } from "./helpers";
 
 const baseClass = "software-card";
 
@@ -187,17 +188,7 @@ const HostSoftware = ({
           "Software is installing or will install when the host comes online."
         );
       } catch (e) {
-        const reason = upperFirst(trimEnd(getErrorReason(e), "."));
-        if (reason.includes("fleetd installed")) {
-          renderFlash("error", `Couldn't install. ${reason}.`);
-        } else if (reason.includes("can be installed only on")) {
-          renderFlash(
-            "error",
-            `Couldn't install. ${reason.replace("darwin", "macOS")}.`
-          );
-        } else {
-          renderFlash("error", "Couldn't install. Please try again.");
-        }
+        renderFlash("error", getErrorMessage(e));
       }
       setInstallingSoftwareId(null);
       refetchSoftware();
diff --git a/frontend/pages/hosts/details/cards/Software/HostSoftwareTableConfig.tsx b/frontend/pages/hosts/details/cards/Software/HostSoftwareTableConfig.tsx
index 0d54533b37..5825f48146 100644
--- a/frontend/pages/hosts/details/cards/Software/HostSoftwareTableConfig.tsx
+++ b/frontend/pages/hosts/details/cards/Software/HostSoftwareTableConfig.tsx
@@ -123,7 +123,7 @@ export const generateSoftwareTableHeaders = ({
       accessor: "name",
       disableSortBy: false,
       Cell: (cellProps: ITableStringCellProps) => {
-        const { id, name, source } = cellProps.row.original;
+        const { id, name, source, app_store_app } = cellProps.row.original;
 
         const softwareTitleDetailsPath = PATHS.SOFTWARE_TITLE_DETAILS(
           id.toString().concat(`?team_id=${teamId}`)
@@ -133,6 +133,7 @@ export const generateSoftwareTableHeaders = ({
           <SoftwareNameCell
             name={name}
             source={source}
+            iconUrl={app_store_app?.icon_url}
             path={softwareTitleDetailsPath}
             router={router}
           />
diff --git a/frontend/pages/hosts/details/cards/Software/helpers.tsx b/frontend/pages/hosts/details/cards/Software/helpers.tsx
new file mode 100644
index 0000000000..e251728bdf
--- /dev/null
+++ b/frontend/pages/hosts/details/cards/Software/helpers.tsx
@@ -0,0 +1,36 @@
+import React from "react";
+import { getErrorReason } from "interfaces/errors";
+import { trimEnd, upperFirst } from "lodash";
+
+const INSTALL_SOFTWARE_ERROR_PREFIX = "Couldn't install.";
+const DEFAULT_ERROR_MESSAGE = `${INSTALL_SOFTWARE_ERROR_PREFIX} Please try again.`;
+
+const createOnlyInstallableOnMacOSMessage = (reason: string) =>
+  `Couldn't install. ${reason.replace("darwin", "macOS")}.`;
+
+const createVPPTokenExpiredMessage = () => (
+  <>
+    {INSTALL_SOFTWARE_ERROR_PREFIX} VPP token expired. Go to{" "}
+    <b>
+      Settings {">"} Integration {">"} Volume Purchasing Program
+    </b>{" "}
+    and renew token.
+  </>
+);
+
+// eslint-disable-next-line import/prefer-default-export
+export const getErrorMessage = (e: unknown) => {
+  const reason = upperFirst(trimEnd(getErrorReason(e), "."));
+
+  if (reason.includes("fleetd installed")) {
+    return `${INSTALL_SOFTWARE_ERROR_PREFIX}. ${reason}.`;
+  } else if (reason.includes("can be installed only on")) {
+    return createOnlyInstallableOnMacOSMessage(reason);
+  } else if (reason.includes("VPP token expired")) {
+    createVPPTokenExpiredMessage();
+  } else if (reason.includes("MDM is turned off")) {
+    return reason;
+  }
+
+  return DEFAULT_ERROR_MESSAGE;
+};