diff --git a/changes/20131-self-service-reinstall b/changes/20131-self-service-reinstall
new file mode 100644
index 0000000000..0891a4a1e9
--- /dev/null
+++ b/changes/20131-self-service-reinstall
@@ -0,0 +1 @@
+- Updated UI to allow device users to reinstall self-service software.
\ No newline at end of file
diff --git a/frontend/pages/hosts/details/cards/Software/SelfService/SelfService.tests.tsx b/frontend/pages/hosts/details/cards/Software/SelfService/SelfService.tests.tsx
index 18179aa90d..60c5ea7d6b 100644
--- a/frontend/pages/hosts/details/cards/Software/SelfService/SelfService.tests.tsx
+++ b/frontend/pages/hosts/details/cards/Software/SelfService/SelfService.tests.tsx
@@ -6,7 +6,23 @@ import mockServer from "test/mock-server";
 import { customDeviceSoftwareHandler } from "test/handlers/device-handler";
 import { createMockDeviceSoftware } from "__mocks__/deviceUserMock";
 
-import SelfService from "./SelfService";
+import SelfService, { ISoftwareSelfServiceProps } from "./SelfService";
+
+const TEST_PROPS: ISoftwareSelfServiceProps = {
+  contactUrl: "http://example.com",
+  deviceToken: "123-456",
+  isSoftwareEnabled: true,
+  pathname: "/test",
+  queryParams: {
+    page: 1,
+    query: "",
+    order_key: "name",
+    order_direction: "asc",
+    per_page: 10,
+    vulnerable: true,
+  },
+  router: createMockRouter(),
+};
 
 describe("SelfService", () => {
   it("should render the self service items correctly", async () => {
@@ -23,23 +39,7 @@ describe("SelfService", () => {
 
     const render = createCustomRenderer({ withBackendMock: true });
 
-    render(
-      <SelfService
-        contactUrl={"http://example.com"}
-        deviceToken={"123-456"}
-        isSoftwareEnabled
-        pathname={"/test"}
-        queryParams={{
-          page: 1,
-          query: "",
-          order_key: "name",
-          order_direction: "asc",
-          per_page: 10,
-          vulnerable: true,
-        }}
-        router={createMockRouter()}
-      />
-    );
+    render(<SelfService {...TEST_PROPS} />);
 
     // waiting for the device software data to render
     await screen.findByText("test1");
@@ -55,6 +55,31 @@ describe("SelfService", () => {
   it("should render the contact link text if contact url is provided", () => {
     mockServer.use(customDeviceSoftwareHandler());
 
+    const render = createCustomRenderer({ withBackendMock: true });
+    render(<SelfService {...TEST_PROPS} router={createMockRouter()} />);
+
+    expect(screen.getByText("reach out to IT")).toBeInTheDocument();
+    expect(screen.getByText("reach out to IT").getAttribute("href")).toBe(
+      "http://example.com"
+    );
+  });
+
+  it("renders 'Reinstall' action button with 'Installed' status", async () => {
+    mockServer.use(
+      customDeviceSoftwareHandler({
+        software: [
+          createMockDeviceSoftware({
+            name: "test-software",
+            status: "installed",
+            last_install: {
+              install_uuid: "test-uuid",
+              installed_at: "2021-08-18T15:11:35Z",
+            },
+          }),
+        ],
+      })
+    );
+
     const render = createCustomRenderer({ withBackendMock: true });
 
     const expectedUrl = "http://example.com";
@@ -77,9 +102,96 @@ describe("SelfService", () => {
       />
     );
 
-    expect(screen.getByText("reach out to IT")).toBeInTheDocument();
-    expect(screen.getByText("reach out to IT").getAttribute("href")).toBe(
-      expectedUrl
+    // waiting for the device software data to render
+    await screen.findByText("test-software");
+
+    expect(
+      screen.getByTestId("self-service-item__status--test")
+    ).toHaveTextContent("Installed");
+
+    expect(
+      screen.getByTestId("self-service-item__item-action-button--test")
+    ).toHaveTextContent("Reinstall");
+  });
+
+  it("renders 'Retry' action button with 'Failed' status", async () => {
+    mockServer.use(
+      customDeviceSoftwareHandler({
+        software: [
+          createMockDeviceSoftware({
+            name: "test-software",
+            status: "failed",
+          }),
+        ],
+      })
     );
+
+    const render = createCustomRenderer({ withBackendMock: true });
+    render(<SelfService {...TEST_PROPS} />);
+
+    // waiting for the device software data to render
+    await screen.findByText("test-software");
+
+    expect(
+      screen.getByTestId("self-service-item__status--test")
+    ).toHaveTextContent("Failed");
+
+    expect(
+      screen.getByTestId("self-service-item__item-action-button--test")
+    ).toHaveTextContent("Retry");
+  });
+
+  it("renders 'Install' action button with no status", async () => {
+    mockServer.use(
+      customDeviceSoftwareHandler({
+        software: [
+          createMockDeviceSoftware({
+            name: "test-software",
+            status: null,
+          }),
+        ],
+      })
+    );
+
+    const render = createCustomRenderer({ withBackendMock: true });
+    render(<SelfService {...TEST_PROPS} />);
+
+    // waiting for the device software data to render
+    await screen.findByText("test-software");
+
+    expect(
+      screen.queryByTestId("self-service-item__status--test")
+    ).not.toBeInTheDocument();
+
+    expect(
+      screen.getByTestId("self-service-item__item-action-button--test")
+    ).toHaveTextContent("Install");
+  });
+
+  it("renders no action button with 'Install in progress...' status", async () => {
+    mockServer.use(
+      customDeviceSoftwareHandler({
+        software: [
+          createMockDeviceSoftware({
+            name: "test-software",
+            status: "pending",
+          }),
+        ],
+      })
+    );
+
+    const render = createCustomRenderer({ withBackendMock: true });
+    render(<SelfService {...TEST_PROPS} />);
+
+    // waiting for the device software data to render
+    await screen.findByText("test-software");
+
+    expect(
+      screen.getByTestId("self-service-item__status--test")
+    ).toHaveTextContent("Install in progress...");
+
+    expect(
+      screen.queryByTestId("self-service-item__item-action-button--test")
+    ).not.toBeInTheDocument();
   });
 });
diff --git a/frontend/pages/hosts/details/cards/Software/SelfService/SelfService.tsx b/frontend/pages/hosts/details/cards/Software/SelfService/SelfService.tsx
index dddc18c49e..f72b02f468 100644
--- a/frontend/pages/hosts/details/cards/Software/SelfService/SelfService.tsx
+++ b/frontend/pages/hosts/details/cards/Software/SelfService/SelfService.tsx
@@ -32,7 +32,7 @@ const DEFAULT_SELF_SERVICE_QUERY_PARAMS = {
   self_service: true,
 } as const;
 
-interface ISoftwareSelfServiceProps {
+export interface ISoftwareSelfServiceProps {
   contactUrl: string;
   deviceToken: string;
   isSoftwareEnabled?: boolean;
diff --git a/frontend/pages/hosts/details/cards/Software/SelfService/SelfServiceItem/SelfServiceItem.tsx b/frontend/pages/hosts/details/cards/Software/SelfService/SelfServiceItem/SelfServiceItem.tsx
index d04e235e66..79befcff85 100644
--- a/frontend/pages/hosts/details/cards/Software/SelfService/SelfServiceItem/SelfServiceItem.tsx
+++ b/frontend/pages/hosts/details/cards/Software/SelfService/SelfServiceItem/SelfServiceItem.tsx
@@ -94,7 +94,9 @@ const InstallerStatus = ({
         data-for={`install-tooltip__${id}`}
       >
         <Icon name={displayConfig.iconName} />
-        <span>{displayConfig.displayText}</span>
+        <span data-testid={`${baseClass}__status--test`}>
+          {displayConfig.displayText}
+        </span>
       </div>
       <ReactTooltip
         className={`${baseClass}__status-tooltip`}
@@ -119,6 +121,20 @@ interface IInstallerStatusActionProps {
   onInstall: () => void;
 }
 
+const getInstallButtonText = (status: SoftwareInstallStatus | null) => {
+  switch (status) {
+    case null:
+      return "Install";
+    case "failed":
+      return "Retry";
+    case "installed":
+      return "Reinstall";
+    default:
+      // we don't show a button for pending installs
+      return "";
+  }
+};
+
 const InstallerStatusAction = ({
   deviceToken,
   software: { id, status, last_install },
@@ -134,6 +150,7 @@ const InstallerStatusAction = ({
   // displayStatus allows us to display the localStatus (if any) or the status from the list
   // software reponse
   const displayStatus = localStatus || status;
+  const installButtonText = getInstallButtonText(displayStatus);
 
   // if the localStatus is "failed", we don't our tooltip to include the old installed_at date so we
   // set this to null, which tells the tooltip to omit the parenthetical date
@@ -172,7 +189,7 @@ const InstallerStatusAction = ({
         />
       </div>
       <div className={`${baseClass}__item-action`}>
-        {(displayStatus === "failed" || displayStatus === null) && (
+        {!!installButtonText && (
           <Button
             variant="text-icon"
             type="button"
@@ -181,7 +198,9 @@ const InstallerStatusAction = ({
             }`}
             onClick={onClick}
           >
-            {displayStatus === "failed" ? "Retry" : "Install"}
+            <span data-testid={`${baseClass}__item-action-button--test`}>
+              {installButtonText}
+            </span>
           </Button>
         )}
       </div>