diff --git a/frontend/pages/hosts/details/OSSettingsModal/OSSettingsTable/OSSettingsErrorCell/OSSettingsErrorCell.tests.tsx b/frontend/pages/hosts/details/OSSettingsModal/OSSettingsTable/OSSettingsErrorCell/OSSettingsErrorCell.tests.tsx
index 3a4ce73d9e..83f0190c14 100644
--- a/frontend/pages/hosts/details/OSSettingsModal/OSSettingsTable/OSSettingsErrorCell/OSSettingsErrorCell.tests.tsx
+++ b/frontend/pages/hosts/details/OSSettingsModal/OSSettingsTable/OSSettingsErrorCell/OSSettingsErrorCell.tests.tsx
@@ -100,4 +100,64 @@ describe("OSSettingsErrorCell", () => {
     expect(screen.getByText(/Learn more/)).toBeInTheDocument();
     expect(screen.getByText(/Learn more/).tagName.toLowerCase()).toBe("a");
   });
+
+  it("renders a formatted tooltip when the error message matches custom scep error patern", () => {
+    render(
+      <OSSettingsErrorCell
+        canResendProfiles
+        hostId={1}
+        profile={createMockHostMdmProfile({
+          status: "failed",
+          detail: `Fleet couldn’t populate $FLEET_VAR_CUSTOM_SCEP_URL_SCEP_WIFI because SCEP_WIFI certificate authority doesn’t exist.`,
+        })}
+      />
+    );
+
+    expect(
+      screen.getByText("Settings > Integrations > Certificates")
+    ).toBeInTheDocument();
+    expect(
+      screen.getByText(/add it and resend the configuration profile/)
+    ).toBeInTheDocument();
+  });
+
+  it("renders a formatted tooltip when the error message matches digicert guid patern", () => {
+    render(
+      <OSSettingsErrorCell
+        canResendProfiles
+        hostId={1}
+        profile={createMockHostMdmProfile({
+          status: "failed",
+          detail: `Couldn’t get certificate from DigiCert. The "profile_id" configured in DIGICERT_WIFI certificate authority doesn’t exist.`,
+        })}
+      />
+    );
+
+    expect(
+      screen.getByText("Settings > Integrations > Certificates")
+    ).toBeInTheDocument();
+    expect(screen.getByText(/correct it and resend/)).toBeInTheDocument();
+    expect(screen.getByText("DIGICERT_WIFI")).toBeInTheDocument();
+    expect(screen.getByText("Profile GUID")).toBeInTheDocument();
+  });
+
+  it("renders a formatted tooltip when the error message matches digicert token patern", () => {
+    render(
+      <OSSettingsErrorCell
+        canResendProfiles
+        hostId={1}
+        profile={createMockHostMdmProfile({
+          status: "failed",
+          detail: `Couldn’t get certificate from DigiCert. The API token configured in DIGICERT_TEST certificate authority is invalid.`,
+        })}
+      />
+    );
+
+    expect(
+      screen.getByText("Settings > Integrations > Certificates")
+    ).toBeInTheDocument();
+    expect(screen.getByText(/correct it and resend/)).toBeInTheDocument();
+    expect(screen.getByText("DIGICERT_TEST")).toBeInTheDocument();
+    expect(screen.getByText("API token")).toBeInTheDocument();
+  });
 });
diff --git a/frontend/pages/hosts/details/OSSettingsModal/OSSettingsTable/OSSettingsErrorCell/OSSettingsErrorCell.tsx b/frontend/pages/hosts/details/OSSettingsModal/OSSettingsTable/OSSettingsErrorCell/OSSettingsErrorCell.tsx
index 1fcc3c00fa..da2b905323 100644
--- a/frontend/pages/hosts/details/OSSettingsModal/OSSettingsTable/OSSettingsErrorCell/OSSettingsErrorCell.tsx
+++ b/frontend/pages/hosts/details/OSSettingsModal/OSSettingsTable/OSSettingsErrorCell/OSSettingsErrorCell.tsx
@@ -6,6 +6,8 @@ import { DEFAULT_EMPTY_CELL_VALUE } from "utilities/constants";
 import hostAPI from "services/entities/hosts";
 import { NotificationContext } from "context/notification";
 
+import { IHostMdmProfile } from "interfaces/mdm";
+
 import TooltipTruncatedTextCell from "components/TableContainer/DataTable/TooltipTruncatedTextCell";
 import Button from "components/buttons/Button";
 import Icon from "components/Icon";
@@ -42,12 +44,99 @@ const RefetchButton = ({ isFetching, onClick }: IRefetchButtonProps) => {
   );
 };
 
+/**
+ * formatDetailCertificateError generates the formatted detail for certain errors related to
+ * certificate profiles. It return a JSX element with the formatted message or null if
+ * the detail does not match any of the expected patterns.
+ */
+const formatDetailCertificateError = (detail: IHostMdmProfile["detail"]) => {
+  const matchTokenErr = detail.match(
+    /get certificate from (?:DigiCert|Digicert|digicert).*token configured in (?<ca>.*) certificate authority is invalid/
+  );
+  if (matchTokenErr?.groups) {
+    return (
+      <>
+        Couldn&apos;t get certificate from DigiCert. The <b>API token</b>{" "}
+        configured in <b>{matchTokenErr.groups.ca}</b> certificate authority is
+        invalid. Please go to{" "}
+        <b>
+          Settings {">"} Integrations {">"} Certificates
+        </b>
+        , correct it and resend.
+      </>
+    );
+  }
+
+  const matchProfileIdErr = detail.match(
+    /get certificate from (?:DigiCert|Digicert|digicert).*profile_id.*configured in (?<ca>.*) certificate authority does(?:n.t| not) exist/
+  );
+  if (matchProfileIdErr?.groups) {
+    return (
+      <>
+        Couldn&apos;t get certificate from DigiCert. The <b>Profile GUID</b>{" "}
+        configured in <b>{matchProfileIdErr.groups.ca}</b> certificate authority
+        doesn&apos;t exist. Please go to{" "}
+        <b>
+          Settings {">"} Integrations {">"} Certificates
+        </b>
+        , correct it and resend.
+      </>
+    );
+  }
+
+  const matchFleetVarErr = detail.match(
+    /populate (?<field>.*) because (?<ca>.*) certificate authority does(?:n.t| not) exist/
+  );
+  if (matchFleetVarErr?.groups) {
+    return (
+      <>
+        Fleet couldn&apos;t populate {matchFleetVarErr.groups.field} because{" "}
+        <b>{matchFleetVarErr.groups.ca}</b> certificate authority doesn&apos;t
+        exist. Please go to{" "}
+        <b>
+          Settings {">"} Integrations {">"} Certificates
+        </b>
+        , add it and resend the configuration profile.
+      </>
+    );
+  }
+
+  return null;
+};
+
+/**
+ * formatDetailIdpEmailError generates the formatted detail for certain errors related to
+ * host IdP email profiles. It returns a JSX element with the formatted message or null if
+ * the detail does not match any of the expected patterns.
+ */
+const formatDetailIdpEmailError = (detail: IHostMdmProfile["detail"]) => {
+  if (detail.includes("There is no IdP email for this host.")) {
+    return (
+      <>
+        There is no IdP email for this host.
+        <br />
+        Fleet couldn&apos;t populate
+        <br />
+        $FLEET_VAR_HOST_END_USER_EMAIL_IDP.
+        <br />
+        <CustomLink
+          text="Learn more"
+          url="https://fleetdm.com/learn-more-about/idp-email"
+          newTab
+          variant="tooltip-link"
+        />
+      </>
+    );
+  }
+  return null;
+};
+
 /**
  * generates the formatted tooltip for the error column.
  * the expected format of the error string is:
  * "key1: value1, key2: value2, key3: value3"
  */
-const generateFormattedTooltip = (detail: string) => {
+const formatDetailWindowsProfile = (detail: string) => {
   const keyValuePairs = detail.split(/, */);
   const formattedElements: JSX.Element[] = [];
 
@@ -90,31 +179,23 @@ const generateErrorTooltip = (
 ) => {
   if (profile.status !== "failed") return null;
 
-  // Special case for creating UI link
-  if (profile.detail.includes("There is no IdP email for this host.")) {
-    return (
-      <>
-        There is no IdP email for this host.
-        <br />
-        Fleet couldn&apos;t populate
-        <br />
-        $FLEET_VAR_HOST_END_USER_EMAIL_IDP.
-        <br />
-        <CustomLink
-          text="Learn more"
-          url="https://fleetdm.com/learn-more-about/idp-email"
-          newTab
-          variant="tooltip-link"
-        />
-      </>
-    );
+  // Special case to handle IdP email errors
+  const idpEmailError = formatDetailIdpEmailError(profile.detail);
+  if (idpEmailError) {
+    return idpEmailError;
   }
 
-  if (profile.platform !== "windows") {
-    return cellValue;
+  // Special case to handle certificate profile errors
+  const certificateError = formatDetailCertificateError(profile.detail);
+  if (certificateError) {
+    return certificateError;
   }
 
-  return generateFormattedTooltip(profile.detail);
+  if (profile.platform === "windows") {
+    return formatDetailWindowsProfile(profile.detail);
+  }
+
+  return cellValue;
 };
 
 interface IOSSettingsErrorCellProps {