diff --git a/changes/24917-installer-url-length b/changes/24917-installer-url-length
new file mode 100644
index 000000000000..af3287c8076f
--- /dev/null
+++ b/changes/24917-installer-url-length
@@ -0,0 +1 @@
+* Increased maximum length for installer URLs specified in GitOps to 4000 characters
diff --git a/ee/server/service/software_installers.go b/ee/server/service/software_installers.go
index 623378d0db92..7c8674068204 100644
--- a/ee/server/service/software_installers.go
+++ b/ee/server/service/software_installers.go
@@ -1154,7 +1154,7 @@ func (svc *Service) BatchSetSoftwareInstallers(
 		if len(payload.URL) > fleet.SoftwareInstallerURLMaxLength {
 			return "", fleet.NewInvalidArgumentError(
 				"software.url",
-				"software URL is too long, must be less than 256 characters",
+				fmt.Sprintf("software URL is too long, must be %d characters or less", fleet.SoftwareInstallerURLMaxLength),
 			)
 		}
 		if _, err := url.ParseRequestURI(payload.URL); err != nil {
diff --git a/pkg/spec/gitops.go b/pkg/spec/gitops.go
index e5f4549182e7..98ed97e9a618 100644
--- a/pkg/spec/gitops.go
+++ b/pkg/spec/gitops.go
@@ -858,7 +858,7 @@ func parseSoftware(top map[string]json.RawMessage, result *GitOps, baseDir strin
 			continue
 		}
 		if len(softwarePackageSpec.URL) > fleet.SoftwareInstallerURLMaxLength {
-			multiError = multierror.Append(multiError, fmt.Errorf("software URL %q is too long, must be less than 256 characters", softwarePackageSpec.URL))
+			multiError = multierror.Append(multiError, fmt.Errorf("software URL %q is too long, must be %d characters or less", softwarePackageSpec.URL, fleet.SoftwareInstallerURLMaxLength))
 			continue
 		}
 		result.Software.Packages = append(result.Software.Packages, &softwarePackageSpec)
diff --git a/pkg/spec/gitops_test.go b/pkg/spec/gitops_test.go
index d32868bbf72f..dfc6703ed5bf 100644
--- a/pkg/spec/gitops_test.go
+++ b/pkg/spec/gitops_test.go
@@ -909,7 +909,7 @@ policies:
 	assert.ErrorContains(t, err, "empty package_path")
 
 	// Software has a URL that's too big
-	tooBigURL := fmt.Sprintf("https://ftp.mozilla.org/%s", strings.Repeat("a", 232))
+	tooBigURL := fmt.Sprintf("https://ftp.mozilla.org/%s", strings.Repeat("a", 4000-23))
 	config = getTeamConfig([]string{"software"})
 	config += fmt.Sprintf(`
 software:
@@ -922,7 +922,7 @@ software:
 	}
 	path, basePath := createTempFile(t, "", config)
 	_, err = GitOpsFromFile(path, basePath, &appConfig, nopLogf)
-	assert.ErrorContains(t, err, fmt.Sprintf("software URL \"%s\" is too long, must be less than 256 characters", tooBigURL))
+	assert.ErrorContains(t, err, fmt.Sprintf("software URL \"%s\" is too long, must be 4000 characters or less", tooBigURL))
 
 	// Policy references a software installer not present in the team.
 	config = getTeamConfig([]string{"policies"})
diff --git a/server/datastore/mysql/migrations/tables/20241219180042_LongInstallerURLs.go b/server/datastore/mysql/migrations/tables/20241219180042_LongInstallerURLs.go
new file mode 100644
index 000000000000..ebecdc190bb5
--- /dev/null
+++ b/server/datastore/mysql/migrations/tables/20241219180042_LongInstallerURLs.go
@@ -0,0 +1,25 @@
+package tables
+
+import (
+	"database/sql"
+	"fmt"
+)
+
+func init() {
+	MigrationClient.AddMigration(Up_20241219180042, Down_20241219180042)
+}
+
+func Up_20241219180042(tx *sql.Tx) error {
+	// The new 'url' column will only be set for software uploaded in batch via GitOps.
+	if _, err := tx.Exec(`
+		ALTER TABLE software_installers
+		CHANGE COLUMN url url VARCHAR(4095) COLLATE utf8mb4_unicode_ci NOT NULL DEFAULT '';
+	`); err != nil {
+		return fmt.Errorf("failed to lengthen url in software_installers: %w", err)
+	}
+	return nil
+}
+
+func Down_20241219180042(tx *sql.Tx) error {
+	return nil
+}
diff --git a/server/datastore/mysql/migrations/tables/20241219180042_LongInstallerURLs_test.go b/server/datastore/mysql/migrations/tables/20241219180042_LongInstallerURLs_test.go
new file mode 100644
index 000000000000..87074c6cfa72
--- /dev/null
+++ b/server/datastore/mysql/migrations/tables/20241219180042_LongInstallerURLs_test.go
@@ -0,0 +1,51 @@
+package tables
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/require"
+)
+
+func TestUp_20241219180042(t *testing.T) {
+	db := applyUpToPrev(t)
+
+	script1 := execNoErrLastID(t, db, "INSERT INTO script_contents(contents, md5_checksum) VALUES ('echo hi', 'a')")
+	script2 := execNoErrLastID(t, db, "INSERT INTO script_contents(contents, md5_checksum) VALUES ('echo bye', 'b')")
+
+	software := execNoErrLastID(t, db, `
+INSERT INTO software_installers (
+  filename,
+  version,
+  platform,
+  install_script_content_id,
+  post_install_script_content_id,
+  uninstall_script_content_id,
+  storage_id,
+  package_ids,
+  url
+) VALUES (
+  'fleet',
+  '1.0.0',
+  'windows',
+  ?,
+  ?,
+  ?,
+  'a',
+  '',
+  ?
+)`, script1, script2, script2, "https://google.com/")
+
+	applyNext(t, db)
+
+	var url string
+	err := db.Get(&url, "SELECT url FROM software_installers WHERE id = ?", software)
+	require.NoError(t, err)
+	require.Equal(t, "https://google.com/", url)
+
+	longUrl := "https://dl.google.com/tag/s/appguid%3D%7B8A69D345-D564-463C-AFF1-A69D9E530F96%7D%26iid%3D%7B53CCDE8D-FD40-46DE-67E7-61E96CFEFCAA%7D%26lang%3Den%26browser%3D4%26usagestats%3D0%26appname%3DGoogle%2520Chrome%26needsadmin%3Dtrue%26ap%3Dx64-stable-statsdef_0%26brand%3DGCEA/dl/chrome/install/googlechromestandaloneenterprise64.msi"
+	execNoErr(t, db, `UPDATE software_installers SET url = ? WHERE id = ?`, longUrl, software)
+
+	err = db.Get(&url, "SELECT url FROM software_installers WHERE id = ?", software)
+	require.NoError(t, err)
+	require.Equal(t, longUrl, url)
+}
diff --git a/server/datastore/mysql/schema.sql b/server/datastore/mysql/schema.sql
index 322fe62b5bf2..2d74123d68cc 100644
--- a/server/datastore/mysql/schema.sql
+++ b/server/datastore/mysql/schema.sql
@@ -1105,9 +1105,9 @@ CREATE TABLE `migration_status_tables` (
   `is_applied` tinyint(1) NOT NULL,
   `tstamp` timestamp NULL DEFAULT CURRENT_TIMESTAMP,
   PRIMARY KEY (`id`)
-) /*!50100 TABLESPACE `innodb_system` */ ENGINE=InnoDB AUTO_INCREMENT=338 DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_unicode_ci;
+) /*!50100 TABLESPACE `innodb_system` */ ENGINE=InnoDB AUTO_INCREMENT=339 DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_unicode_ci;
 /*!40101 SET character_set_client = @saved_cs_client */;
-INSERT INTO `migration_status_tables` VALUES (1,0,1,'2020-01-01 01:01:01'),(2,20161118193812,1,'2020-01-01 01:01:01'),(3,20161118211713,1,'2020-01-01 01:01:01'),(4,20161118212436,1,'2020-01-01 01:01:01'),(5,20161118212515,1,'2020-01-01 01:01:01'),(6,20161118212528,1,'2020-01-01 01:01:01'),(7,20161118212538,1,'2020-01-01 01:01:01'),(8,20161118212549,1,'2020-01-01 01:01:01'),(9,20161118212557,1,'2020-01-01 01:01:01'),(10,20161118212604,1,'2020-01-01 01:01:01'),(11,20161118212613,1,'2020-01-01 01:01:01'),(12,20161118212621,1,'2020-01-01 01:01:01'),(13,20161118212630,1,'2020-01-01 01:01:01'),(14,20161118212641,1,'2020-01-01 01:01:01'),(15,20161118212649,1,'2020-01-01 01:01:01'),(16,20161118212656,1,'2020-01-01 01:01:01'),(17,20161118212758,1,'2020-01-01 01:01:01'),(18,20161128234849,1,'2020-01-01 01:01:01'),(19,20161230162221,1,'2020-01-01 01:01:01'),(20,20170104113816,1,'2020-01-01 01:01:01'),(21,20170105151732,1,'2020-01-01 01:01:01'),(22,20170108191242,1,'2020-01-01 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 /*!40101 SET @saved_cs_client     = @@character_set_client */;
 /*!50503 SET character_set_client = utf8mb4 */;
 CREATE TABLE `mobile_device_management_solutions` (
@@ -1808,7 +1808,7 @@ CREATE TABLE `software_installers` (
   `user_id` int unsigned DEFAULT NULL,
   `user_name` varchar(255) CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci NOT NULL DEFAULT '',
   `user_email` varchar(255) CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci NOT NULL DEFAULT '',
-  `url` varchar(255) CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci NOT NULL DEFAULT '',
+  `url` varchar(4095) CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci NOT NULL DEFAULT '',
   `package_ids` text CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci NOT NULL,
   `extension` varchar(32) CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci NOT NULL DEFAULT '',
   `uninstall_script_content_id` int unsigned NOT NULL,
diff --git a/server/fleet/software_installer.go b/server/fleet/software_installer.go
index c1e376cc8dbc..82966a2c5d1f 100644
--- a/server/fleet/software_installer.go
+++ b/server/fleet/software_installer.go
@@ -548,7 +548,7 @@ type SoftwareInstallerTokenMetadata struct {
 	TeamID  uint `json:"team_id"`
 }
 
-const SoftwareInstallerURLMaxLength = 255
+const SoftwareInstallerURLMaxLength = 4000
 
 // TempFileReader is an io.Reader with all extra io interfaces supported by a
 // file on disk reader (e.g. io.ReaderAt, io.Seeker, etc.). When created with
diff --git a/server/service/integration_enterprise_test.go b/server/service/integration_enterprise_test.go
index 56b71fb1f85a..97d4e0e7d8b0 100644
--- a/server/service/integration_enterprise_test.go
+++ b/server/service/integration_enterprise_test.go
@@ -11237,7 +11237,7 @@ func (s *integrationEnterpriseTestSuite) TestBatchSetSoftwareInstallers() {
 
 	// software with a too big URL
 	softwareToInstall = []fleet.SoftwareInstallerPayload{
-		{URL: "https://ftp.mozilla.org/" + strings.Repeat("a", 233)},
+		{URL: "https://ftp.mozilla.org/" + strings.Repeat("a", 4000-23)},
 	}
 	s.Do("POST", "/api/latest/fleet/software/batch", batchSetSoftwareInstallersRequest{Software: softwareToInstall}, http.StatusUnprocessableEntity, "team_name", tm.Name)