diff --git a/changes/26114-new-team-with-vpp-apps b/changes/26114-new-team-with-vpp-apps
new file mode 100644
index 0000000000..6a0233d03f
--- /dev/null
+++ b/changes/26114-new-team-with-vpp-apps
@@ -0,0 +1 @@
+Fixed `fleetctl gitops` issue where creating a new team containing VPP apps caused an error.
diff --git a/cmd/fleetctl/gitops.go b/cmd/fleetctl/gitops.go
index 2af554fde1..a4e7584a61 100644
--- a/cmd/fleetctl/gitops.go
+++ b/cmd/fleetctl/gitops.go
@@ -15,7 +15,10 @@ import (
 	"golang.org/x/text/unicode/norm"
 )
 
-const filenameMaxLength = 255
+const (
+	filenameMaxLength           = 255
+	reapplyingTeamForVPPAppsMsg = "[!] re-applying configs for team %s -- this only happens once for new teams that have VPP apps\n"
+)
 
 type LabelUsage struct {
 	Name string
@@ -96,8 +99,14 @@ func gitopsCommand() *cli.Command {
 			var originalVPPConfig []any
 			var teamNames []string
 			var teamDryRunAssumptions *fleet.TeamSpecsDryRunAssumptions
-			var abmTeams, vppTeams []string
-			var hasMissingABMTeam, hasMissingVPPTeam, usesLegacyABMConfig bool
+			var abmTeams, vppTeams, missingVPPTeams []string
+			var hasMissingABMTeam, usesLegacyABMConfig bool
+			type missingVPPTeamWithApps struct {
+				config   *spec.GitOps
+				vppApps  []*fleet.TeamSpecAppStoreApp
+				filename string
+			}
+			var missingVPPTeamsWithApps []missingVPPTeamWithApps
 
 			// we keep track of team software installers and scripts for correct policy application
 			teamsSoftwareInstallers := make(map[string][]fleet.SoftwarePackageResponse)
@@ -233,7 +242,7 @@ func gitopsCommand() *cli.Command {
 						return err
 					}
 
-					vppTeams, hasMissingVPPTeam, err = checkVPPTeamAssignments(config, fleetClient)
+					vppTeams, missingVPPTeams, err = checkVPPTeamAssignments(config, fleetClient)
 					if err != nil {
 						return err
 					}
@@ -258,7 +267,7 @@ func gitopsCommand() *cli.Command {
 						}
 					}
 
-					if hasMissingVPPTeam {
+					if len(missingVPPTeams) > 0 {
 						if mdm, ok := config.OrgSettings["mdm"]; ok {
 							if mdmMap, ok := mdm.(map[string]any); ok {
 								if vpp, ok := mdmMap["volume_purchasing_program"]; ok {
@@ -275,6 +284,21 @@ func gitopsCommand() *cli.Command {
 					}
 				}
 
+				// We cannot apply a VPP app to a new team until that team gets a VPP token.
+				// So, we create the team, then apply the VPP token, then apply VPP apps.
+				if !isGlobalConfig && len(missingVPPTeams) > 0 && len(config.Software.AppStoreApps) > 0 {
+					for _, missingTeam := range missingVPPTeams {
+						if missingTeam == *config.TeamName {
+							missingVPPTeamsWithApps = append(missingVPPTeamsWithApps, missingVPPTeamWithApps{
+								config:   config,
+								vppApps:  config.Software.AppStoreApps,
+								filename: flFilename,
+							})
+							config.Software.AppStoreApps = nil
+						}
+					}
+				}
+
 				if flDryRun {
 					incomingSecrets := fleetClient.GetGitOpsSecrets(config)
 					for _, secret := range incomingSecrets {
@@ -308,11 +332,23 @@ func gitopsCommand() *cli.Command {
 					return err
 				}
 			}
-			if len(vppTeams) > 0 && hasMissingVPPTeam {
+			if len(missingVPPTeams) > 0 {
 				if err = applyVPPTokenAssignmentIfNeeded(c, teamNames, vppTeams, originalVPPConfig, flDryRun, fleetClient); err != nil {
 					return err
 				}
 			}
+			// Now that VPP tokens have been assigned, we can apply VPP apps to the new team.
+			// For simplicity, we simply re-apply the entire config. This only happens once when the team is created.
+			for _, teamWithApps := range missingVPPTeamsWithApps {
+				_, _ = fmt.Fprintf(c.App.Writer, reapplyingTeamForVPPAppsMsg, *teamWithApps.config.TeamName)
+				teamWithApps.config.Software.AppStoreApps = teamWithApps.vppApps
+				_, err := fleetClient.DoGitOps(c.Context, teamWithApps.config, teamWithApps.filename, logf, flDryRun, teamDryRunAssumptions, appConfig,
+					teamsSoftwareInstallers, teamsVPPApps, teamsScripts)
+				if err != nil {
+					return err
+				}
+			}
+
 			if flDeleteOtherTeams && appConfig.License.IsPremium() { // skip team deletion for non-premium users
 				teams, err := fleetClient.ListTeams("")
 				if err != nil {
@@ -621,13 +657,13 @@ func applyABMTokenAssignmentIfNeeded(
 }
 
 func checkVPPTeamAssignments(config *spec.GitOps, fleetClient *service.Client) (
-	vppTeams []string, missingTeam bool, err error,
+	vppTeams []string, missingTeams []string, err error,
 ) {
 	if mdm, ok := config.OrgSettings["mdm"]; ok {
 		if mdmMap, ok := mdm.(map[string]any); ok {
 			teams, err := fleetClient.ListTeams("")
 			if err != nil {
-				return nil, false, err
+				return nil, nil, err
 			}
 			teamNames := map[string]struct{}{}
 			for _, tm := range teams {
@@ -645,7 +681,7 @@ func checkVPPTeamAssignments(config *spec.GitOps, fleetClient *service.Client) (
 										normalizedTeam := norm.NFC.String(teamStr)
 										vppTeams = append(vppTeams, normalizedTeam)
 										if _, ok := teamNames[normalizedTeam]; !ok {
-											missingTeam = true
+											missingTeams = append(missingTeams, normalizedTeam)
 										}
 									}
 								}
@@ -657,7 +693,7 @@ func checkVPPTeamAssignments(config *spec.GitOps, fleetClient *service.Client) (
 		}
 	}
 
-	return vppTeams, missingTeam, nil
+	return vppTeams, missingTeams, nil
 }
 
 func applyVPPTokenAssignmentIfNeeded(
diff --git a/cmd/fleetctl/gitops_test.go b/cmd/fleetctl/gitops_test.go
index f9a61f861d..6dd3d54f29 100644
--- a/cmd/fleetctl/gitops_test.go
+++ b/cmd/fleetctl/gitops_test.go
@@ -2,6 +2,7 @@ package main
 
 import (
 	"context"
+	"database/sql"
 	"encoding/json"
 	"fmt"
 	"net/http"
@@ -2785,6 +2786,60 @@ func TestGitOpsTeamVPPApps(t *testing.T) {
 	}
 }
 
+// TestGitOpsTeamVPPAndApp tests the flow where a new team is created with VPP apps.
+// GitOps must first create the team, then assign VPP token to it, and only then add VPP apps.
+func TestGitOpsTeamVPPAndApp(t *testing.T) {
+	startAndServeVPPServer(t)
+	ds, _, _ := setupFullGitOpsPremiumServer(t)
+	renewDate := time.Now().Add(24 * time.Hour)
+	token, err := test.CreateVPPTokenEncoded(renewDate, "fleet", "ca")
+	require.NoError(t, err)
+
+	ds.GetVPPAppsFunc = func(ctx context.Context, teamID *uint) ([]fleet.VPPAppResponse, error) {
+		return []fleet.VPPAppResponse{}, nil
+	}
+	ds.GetABMTokenCountFunc = func(ctx context.Context) (int, error) {
+		return 0, nil
+	}
+
+	// The following mocks are key to this test.
+	vppToken := &fleet.VPPTokenDB{
+		ID:        1,
+		OrgName:   "Fleet",
+		Location:  "Earth",
+		RenewDate: renewDate,
+		Token:     string(token),
+		Teams:     nil,
+	}
+	tokensByTeams := make(map[uint]*fleet.VPPTokenDB)
+	ds.UpdateVPPTokenTeamsFunc = func(ctx context.Context, id uint, teams []uint) (*fleet.VPPTokenDB, error) {
+		for _, teamID := range teams {
+			tokensByTeams[teamID] = vppToken
+		}
+		return vppToken, nil
+	}
+	ds.ListVPPTokensFunc = func(ctx context.Context) ([]*fleet.VPPTokenDB, error) {
+		return []*fleet.VPPTokenDB{vppToken}, nil
+	}
+	ds.GetVPPTokenByTeamIDFunc = func(ctx context.Context, teamID *uint) (*fleet.VPPTokenDB, error) {
+		if teamID == nil {
+			return vppToken, nil
+		}
+		token, ok := tokensByTeams[*teamID]
+		if !ok {
+			return nil, sql.ErrNoRows
+		}
+		return token, nil
+	}
+
+	buf, err := runAppNoChecks([]string{"gitops", "-f", "testdata/gitops/global_config_vpp.yml", "-f", "testdata/gitops/team_vpp_valid_app.yml"})
+	require.NoError(t, err)
+	assert.True(t, ds.UpdateVPPTokenTeamsFuncInvoked)
+	assert.True(t, ds.GetVPPTokenByTeamIDFuncInvoked)
+	assert.True(t, ds.SetTeamVPPAppsFuncInvoked)
+	assert.Contains(t, buf.String(), fmt.Sprintf(reapplyingTeamForVPPAppsMsg, teamName))
+}
+
 func TestGitOpsCustomSettings(t *testing.T) {
 	cases := []struct {
 		file    string
@@ -3185,6 +3240,17 @@ func setupFullGitOpsPremiumServer(t *testing.T) (*mock.Store, **fleet.AppConfig,
 		}
 		return nil, nil
 	}
+	ds.TeamsSummaryFunc = func(ctx context.Context) ([]*fleet.TeamSummary, error) {
+		summary := make([]*fleet.TeamSummary, 0, len(savedTeams))
+		for _, team := range savedTeams {
+			summary = append(summary, &fleet.TeamSummary{
+				ID:          (*team).ID,
+				Name:        (*team).Name,
+				Description: (*team).Description,
+			})
+		}
+		return summary, nil
+	}
 	ds.ListQueriesFunc = func(ctx context.Context, opts fleet.ListQueryOptions) ([]*fleet.Query, int, *fleet.PaginationMetadata, error) {
 		return nil, 0, nil, nil
 	}
diff --git a/cmd/fleetctl/testdata/gitops/global_config_vpp.yml b/cmd/fleetctl/testdata/gitops/global_config_vpp.yml
new file mode 100644
index 0000000000..0d5c9c9d39
--- /dev/null
+++ b/cmd/fleetctl/testdata/gitops/global_config_vpp.yml
@@ -0,0 +1,16 @@
+policies:
+queries:
+agent_options:
+controls:
+org_settings:
+  mdm:
+    volume_purchasing_program:
+      - location: Earth
+        teams:
+          - "${TEST_TEAM_NAME}"
+  server_settings:
+    server_url: https://example.com
+  org_info:
+    org_name: Fleet
+  secrets:
+    - secret: "FLEET_GLOBAL_ENROLL_SECRET"