diff --git a/changes/37597-ignore-build-version-compare b/changes/37597-ignore-build-version-compare
new file mode 100644
index 0000000000..77a479bda2
--- /dev/null
+++ b/changes/37597-ignore-build-version-compare
@@ -0,0 +1 @@
+- Fleet UI: Ignore parenthesized build numbers when comparing versions for update availability (e.g. 5.0 (build 3400))
diff --git a/frontend/pages/hosts/details/cards/Software/helpers.tests.ts b/frontend/pages/hosts/details/cards/Software/helpers.tests.ts
index 7465c58445..d5c1ffdcba 100644
--- a/frontend/pages/hosts/details/cards/Software/helpers.tests.ts
+++ b/frontend/pages/hosts/details/cards/Software/helpers.tests.ts
@@ -59,8 +59,19 @@ describe("compareVersions", () => {
     expect(compareVersions("v2.0.0", "v1.0.0")).toBe(1);
   });
 
-  it("treats build metadata as equal (if supported)", () => {
+  it("treats build metadata as equal", () => {
     expect(compareVersions("1.0.0+20130313144700", "1.0.0")).toBe(0);
+    expect(compareVersions("1.0.0+exp.sha.5114f85", "1.0.0+21AF26D3")).toBe(0);
+  });
+
+  it("treats build metadata as equal even with prerelease", () => {
+    expect(compareVersions("1.0.0-alpha+001", "1.0.0-alpha+exp.sha")).toBe(0);
+  });
+
+  it("orders prerelease regardless of build metadata", () => {
+    // same core, prerelease different, builds ignored
+    expect(compareVersions("1.0.0-alpha+001", "1.0.0-beta+exp.sha")).toBe(-1);
+    expect(compareVersions("1.0.0-rc+build.1", "1.0.0+build.2")).toBe(-1);
   });
 
   it("is case-insensitive for pre-release tags", () => {
@@ -73,8 +84,31 @@ describe("compareVersions", () => {
     expect(compareVersions("01.1.0", "1.1.0")).toBe(0);
   });
 
-  it("compares build number in parentheses", () => {
-    expect(compareVersions("6.1.11 (39163)", "6.1.11 (30000)")).toBe(1);
+  // Parenthesized build metadata cases
+  it("treats parenthesized build number as metadata (same core)", () => {
+    expect(compareVersions("8.0 (build 6300)", "8.0")).toBe(0);
+    expect(compareVersions("8.0 (build 6300)", "8.0 (build 7000)")).toBe(0);
+  });
+
+  it("compares different core versions ignoring parenthesized build", () => {
+    expect(compareVersions("8.1 (build 6300)", "8.0")).toBe(1);
+    expect(compareVersions("8.0", "8.1 (build 6300)")).toBe(-1);
+    expect(compareVersions("6.1.12 (39163)", "6.1.11 (30000)")).toBe(1);
+  });
+
+  it("handles mixed +build and parenthesized build metadata", () => {
+    expect(compareVersions("1.0.0+20130313144700", "1.0.0 (build 1234)")).toBe(
+      0
+    );
+    expect(
+      compareVersions("2.3.4-beta+exp.sha", "2.3.4-beta (build 9999)")
+    ).toBe(0);
+  });
+
+  it("handles unexpected parenthesis content as build metadata suffix", () => {
+    // ignore any trailing `(build ...)` suffix
+    expect(compareVersions("1.2.3 (Build 5)", "1.2.3")).toBe(0);
+    expect(compareVersions("1.2.3 (build foo-bar)", "1.2.3")).toBe(0);
   });
 });
 
diff --git a/frontend/pages/hosts/details/cards/Software/helpers.tsx b/frontend/pages/hosts/details/cards/Software/helpers.tsx
index 88dc9bb9e0..6d78d9367f 100644
--- a/frontend/pages/hosts/details/cards/Software/helpers.tsx
+++ b/frontend/pages/hosts/details/cards/Software/helpers.tsx
@@ -30,9 +30,23 @@ export const getHostSoftwareFilterFromQueryParams = (
 const PRE_RELEASE_ORDER = ["alpha", "beta", "rc", ""];
 
 /**
- * Removes build metadata from a version string (e.g., "1.0.0+build" -> "1.0.0").
+ * Removes build metadata and parenthesized build info from a version string.
+ * Examples:
+ *   "1.0.0+build.1"        -> "1.0.0"
+ *   "8.0 (build 6300)"     -> "8.0"
+ *   "8.1.2 (Build 6300)"   -> "8.1.2"
  */
-const stripBuildMetadata = (version: string): string => version.split("+")[0];
+const stripBuildMetadata = (version: string): string => {
+  if (typeof version !== "string") {
+    return "";
+  }
+
+  // First drop any parenthesized "build ..." suffix, e.g. "8.0 (build 6300)" -> "8.0"
+  const withoutParenBuild = version.replace(/\s*\(build\s+[^)]+\)\s*$/i, "");
+
+  // Then drop standard SemVer +build metadata, e.g. "1.0.0+build.1" -> "1.0.0"
+  return withoutParenBuild.split("+")[0];
+};
 
 /**
  * Splits a version string into an array of numeric and string segments.