diff --git a/apps/web/src/app/admin-console/organizations/members/components/member-dialog/member-dialog.component.ts b/apps/web/src/app/admin-console/organizations/members/components/member-dialog/member-dialog.component.ts
index 91d0fc97e6..f449b7f206 100644
--- a/apps/web/src/app/admin-console/organizations/members/components/member-dialog/member-dialog.component.ts
+++ b/apps/web/src/app/admin-console/organizations/members/components/member-dialog/member-dialog.component.ts
@@ -35,6 +35,7 @@ import {
 } from "../../../shared/components/access-selector";
 
 import { commaSeparatedEmails } from "./validators/comma-separated-emails.validator";
+import { freeOrgSeatLimitReachedValidator } from "./validators/free-org-inv-limit-reached.validator";
 
 export enum MemberDialogTab {
   Role = 0,
@@ -46,6 +47,7 @@ export interface MemberDialogParams {
   name: string;
   organizationId: string;
   organizationUserId: string;
+  allOrganizationUserEmails: string[];
   usesKeyConnector: boolean;
   initialTab?: MemberDialogTab;
 }
@@ -79,7 +81,7 @@ export class MemberDialogComponent implements OnInit, OnDestroy {
   protected groupAccessItems: AccessItemView[] = [];
   protected tabIndex: MemberDialogTab;
   protected formGroup = this.formBuilder.group({
-    emails: ["", [Validators.required, commaSeparatedEmails]],
+    emails: ["", { updateOn: "blur" }],
     type: OrganizationUserType.User,
     externalId: this.formBuilder.control({ value: "", disabled: true }),
     accessAllCollections: false,
@@ -167,6 +169,20 @@ export class MemberDialogComponent implements OnInit, OnDestroy {
         this.canUseCustomPermissions = organization.useCustomPermissions;
         this.canUseSecretsManager = organization.useSecretsManager && flagEnabled("secretsManager");
 
+        const emailsControlValidators = [
+          Validators.required,
+          commaSeparatedEmails,
+          freeOrgSeatLimitReachedValidator(
+            this.organization,
+            this.params.allOrganizationUserEmails,
+            this.i18nService.t("subscriptionFreePlan", organization.seats)
+          ),
+        ];
+
+        const emailsControl = this.formGroup.get("emails");
+        emailsControl.setValidators(emailsControlValidators);
+        emailsControl.updateValueAndValidity();
+
         this.collectionAccessItems = [].concat(
           collections.map((c) => mapCollectionToAccessItemView(c))
         );
diff --git a/apps/web/src/app/admin-console/organizations/members/components/member-dialog/validators/free-org-inv-limit-reached.validator.spec.ts b/apps/web/src/app/admin-console/organizations/members/components/member-dialog/validators/free-org-inv-limit-reached.validator.spec.ts
new file mode 100644
index 0000000000..5c17a128ac
--- /dev/null
+++ b/apps/web/src/app/admin-console/organizations/members/components/member-dialog/validators/free-org-inv-limit-reached.validator.spec.ts
@@ -0,0 +1,106 @@
+import { AbstractControl, FormControl, ValidationErrors } from "@angular/forms";
+
+import { OrganizationUserType } from "@bitwarden/common/admin-console/enums";
+import { Organization } from "@bitwarden/common/admin-console/models/domain/organization";
+import { ProductType } from "@bitwarden/common/enums";
+
+import { freeOrgSeatLimitReachedValidator } from "./free-org-inv-limit-reached.validator";
+
+const orgFactory = (props: Partial<Organization> = {}) =>
+  Object.assign(
+    new Organization(),
+    {
+      id: "myOrgId",
+      enabled: true,
+      type: OrganizationUserType.Admin,
+    },
+    props
+  );
+
+describe("freeOrgSeatLimitReachedValidator", () => {
+  let organization: Organization;
+  let allOrganizationUserEmails: string[];
+  let validatorFn: (control: AbstractControl) => ValidationErrors | null;
+
+  beforeEach(() => {
+    allOrganizationUserEmails = ["user1@example.com"];
+  });
+
+  it("should return null when control value is empty", () => {
+    validatorFn = freeOrgSeatLimitReachedValidator(
+      organization,
+      allOrganizationUserEmails,
+      "You cannot invite more than 2 members without upgrading your plan."
+    );
+    const control = new FormControl("");
+
+    const result = validatorFn(control);
+
+    expect(result).toBeNull();
+  });
+
+  it("should return null when control value is null", () => {
+    validatorFn = freeOrgSeatLimitReachedValidator(
+      organization,
+      allOrganizationUserEmails,
+      "You cannot invite more than 2 members without upgrading your plan."
+    );
+    const control = new FormControl(null);
+
+    const result = validatorFn(control);
+
+    expect(result).toBeNull();
+  });
+
+  it("should return null when max seats are not exceeded on free plan", () => {
+    organization = orgFactory({
+      planProductType: ProductType.Free,
+      seats: 2,
+    });
+    validatorFn = freeOrgSeatLimitReachedValidator(
+      organization,
+      allOrganizationUserEmails,
+      "You cannot invite more than 2 members without upgrading your plan."
+    );
+    const control = new FormControl("user2@example.com");
+
+    const result = validatorFn(control);
+
+    expect(result).toBeNull();
+  });
+
+  it("should return validation error when max seats are exceeded on free plan", () => {
+    organization = orgFactory({
+      planProductType: ProductType.Free,
+      seats: 2,
+    });
+    const errorMessage = "You cannot invite more than 2 members without upgrading your plan.";
+    validatorFn = freeOrgSeatLimitReachedValidator(
+      organization,
+      allOrganizationUserEmails,
+      "You cannot invite more than 2 members without upgrading your plan."
+    );
+    const control = new FormControl("user2@example.com,user3@example.com");
+
+    const result = validatorFn(control);
+
+    expect(result).toStrictEqual({ freePlanLimitReached: { message: errorMessage } });
+  });
+
+  it("should return null when not on free plan", () => {
+    const control = new FormControl("user2@example.com,user3@example.com");
+    organization = orgFactory({
+      planProductType: ProductType.Enterprise,
+      seats: 100,
+    });
+    validatorFn = freeOrgSeatLimitReachedValidator(
+      organization,
+      allOrganizationUserEmails,
+      "You cannot invite more than 2 members without upgrading your plan."
+    );
+
+    const result = validatorFn(control);
+
+    expect(result).toBeNull();
+  });
+});
diff --git a/apps/web/src/app/admin-console/organizations/members/components/member-dialog/validators/free-org-inv-limit-reached.validator.ts b/apps/web/src/app/admin-console/organizations/members/components/member-dialog/validators/free-org-inv-limit-reached.validator.ts
new file mode 100644
index 0000000000..6d5c45a64d
--- /dev/null
+++ b/apps/web/src/app/admin-console/organizations/members/components/member-dialog/validators/free-org-inv-limit-reached.validator.ts
@@ -0,0 +1,36 @@
+import { AbstractControl, ValidationErrors, ValidatorFn } from "@angular/forms";
+
+import { Organization } from "@bitwarden/common/admin-console/models/domain/organization";
+import { ProductType } from "@bitwarden/common/enums";
+
+/**
+ * Checks if the limit of free organization seats has been reached when adding new users
+ * @param organization An object representing the organization
+ * @param allOrganizationUserEmails An array of strings with existing user email addresses
+ * @param errorMessage A localized string to display if validation fails
+ * @returns A function that validates an `AbstractControl` and returns `ValidationErrors` or `null`
+ */
+export function freeOrgSeatLimitReachedValidator(
+  organization: Organization,
+  allOrganizationUserEmails: string[],
+  errorMessage: string
+): ValidatorFn {
+  return (control: AbstractControl): ValidationErrors | null => {
+    if (control.value === "" || !control.value) {
+      return null;
+    }
+
+    const newEmailsToAdd = control.value
+      .split(",")
+      .filter(
+        (newEmailToAdd: string) =>
+          newEmailToAdd &&
+          !allOrganizationUserEmails.some((existingEmail) => existingEmail === newEmailToAdd)
+      );
+
+    return organization.planProductType === ProductType.Free &&
+      allOrganizationUserEmails.length + newEmailsToAdd.length > organization.seats
+      ? { freePlanLimitReached: { message: errorMessage } }
+      : null;
+  };
+}
diff --git a/apps/web/src/app/admin-console/organizations/members/people.component.ts b/apps/web/src/app/admin-console/organizations/members/people.component.ts
index 58a02274f8..e7d9bf6772 100644
--- a/apps/web/src/app/admin-console/organizations/members/people.component.ts
+++ b/apps/web/src/app/admin-console/organizations/members/people.component.ts
@@ -396,6 +396,7 @@ export class PeopleComponent
         name: this.userNamePipe.transform(user),
         organizationId: this.organization.id,
         organizationUserId: user != null ? user.id : null,
+        allOrganizationUserEmails: this.allUsers?.map((user) => user.email) ?? [],
         usesKeyConnector: user?.usesKeyConnector,
         initialTab: initialTab,
       },