diff --git a/Common/Models/DatabaseModels/IncidentRole.ts b/Common/Models/DatabaseModels/IncidentRole.ts
index fac37da9f3..b419b0f25c 100644
--- a/Common/Models/DatabaseModels/IncidentRole.ts
+++ b/Common/Models/DatabaseModels/IncidentRole.ts
@@ -493,4 +493,38 @@ export default class IncidentRole extends BaseModel {
     default: true,
   })
   public isDeleteable?: boolean = undefined;
+
+  @ColumnAccessControl({
+    create: [
+      Permission.ProjectOwner,
+      Permission.ProjectAdmin,
+      Permission.ProjectMember,
+      Permission.CreateIncidentRole,
+    ],
+    read: [
+      Permission.ProjectOwner,
+      Permission.ProjectAdmin,
+      Permission.ProjectMember,
+      Permission.ReadIncidentRole,
+      Permission.ReadAllProjectResources,
+    ],
+    update: [
+      Permission.ProjectOwner,
+      Permission.ProjectAdmin,
+      Permission.ProjectMember,
+      Permission.EditIncidentRole,
+    ],
+  })
+  @TableColumn({
+    isDefaultValueColumn: true,
+    type: TableColumnType.Boolean,
+    title: "Can Assign Multiple Users",
+    description:
+      "Can multiple users be assigned to this role? If false, only one user can be assigned.",
+  })
+  @Column({
+    type: ColumnType.Boolean,
+    default: false,
+  })
+  public canAssignMultipleUsers?: boolean = undefined;
 }
diff --git a/Common/Server/Infrastructure/Postgres/SchemaMigrations/1769802715014-MigrationName.ts b/Common/Server/Infrastructure/Postgres/SchemaMigrations/1769802715014-MigrationName.ts
new file mode 100644
index 0000000000..a6987a41ce
--- /dev/null
+++ b/Common/Server/Infrastructure/Postgres/SchemaMigrations/1769802715014-MigrationName.ts
@@ -0,0 +1,17 @@
+import { MigrationInterface, QueryRunner } from "typeorm";
+
+export class MigrationName1769802715014 implements MigrationInterface {
+  public name = "MigrationName1769802715014";
+
+  public async up(queryRunner: QueryRunner): Promise<void> {
+    await queryRunner.query(
+      `ALTER TABLE "IncidentRole" ADD "canAssignMultipleUsers" boolean NOT NULL DEFAULT false`,
+    );
+  }
+
+  public async down(queryRunner: QueryRunner): Promise<void> {
+    await queryRunner.query(
+      `ALTER TABLE "IncidentRole" DROP COLUMN "canAssignMultipleUsers"`,
+    );
+  }
+}
diff --git a/Common/Server/Infrastructure/Postgres/SchemaMigrations/Index.ts b/Common/Server/Infrastructure/Postgres/SchemaMigrations/Index.ts
index b0f95ed848..df36f39e1c 100644
--- a/Common/Server/Infrastructure/Postgres/SchemaMigrations/Index.ts
+++ b/Common/Server/Infrastructure/Postgres/SchemaMigrations/Index.ts
@@ -247,6 +247,7 @@ import { MigrationName1769723982900 } from "./1769723982900-MigrationName";
 import { MigrationName1769772215532 } from "./1769772215532-MigrationName";
 import { MigrationName1769774527481 } from "./1769774527481-MigrationName";
 import { MigrationName1769780297584 } from "./1769780297584-MigrationName";
+import { MigrationName1769802715014 } from "./1769802715014-MigrationName";
 
 export default [
   InitialMigration,
@@ -498,4 +499,5 @@ export default [
   MigrationName1769772215532,
   MigrationName1769774527481,
   MigrationName1769780297584,
+  MigrationName1769802715014,
 ];
diff --git a/Common/Server/Services/ProjectService.ts b/Common/Server/Services/ProjectService.ts
index 6092f9c867..25a26c7e0d 100755
--- a/Common/Server/Services/ProjectService.ts
+++ b/Common/Server/Services/ProjectService.ts
@@ -1006,6 +1006,7 @@ export class ProjectService extends DatabaseService<Model> {
     observer.color = Gray500;
     observer.roleIcon = IconProp.Activity;
     observer.projectId = createdItem.id!;
+    observer.canAssignMultipleUsers = true;
 
     observer = await IncidentRoleService.create({
       data: observer,
diff --git a/Common/UI/Components/MemberRoleAssignment/MemberRoleAssignment.tsx b/Common/UI/Components/MemberRoleAssignment/MemberRoleAssignment.tsx
index d744fec504..b0aa163906 100644
--- a/Common/UI/Components/MemberRoleAssignment/MemberRoleAssignment.tsx
+++ b/Common/UI/Components/MemberRoleAssignment/MemberRoleAssignment.tsx
@@ -24,6 +24,7 @@ export interface MemberRole {
   color: Color;
   isPrimaryRole?: boolean;
   icon?: IconProp;
+  canAssignMultipleUsers?: boolean;
 }
 
 export interface AssignedMember {
@@ -108,28 +109,39 @@ const MemberRoleAssignment: FunctionComponent<ComponentProps> = (
     [props.onUnassignMember],
   );
 
-  // Get member for a specific role (only one per role)
-  const getMemberForRole: (roleId: ObjectID) => AssignedMember | null =
+  // Get members for a specific role
+  const getMembersForRole: (roleId: ObjectID) => Array<AssignedMember> =
     useCallback(
-      (roleId: ObjectID): AssignedMember | null => {
-        return (
-          props.assignedMembers.find((member: AssignedMember) => {
-            return member.roleId.toString() === roleId.toString();
-          }) || null
-        );
+      (roleId: ObjectID): Array<AssignedMember> => {
+        return props.assignedMembers.filter((member: AssignedMember) => {
+          return member.roleId.toString() === roleId.toString();
+        });
       },
       [props.assignedMembers],
     );
 
-  const getUserDropdownOptions: () => Array<DropdownOption> =
-    useCallback((): Array<DropdownOption> => {
-      return props.availableUsers.map((user: AvailableUser) => {
-        return {
-          value: user.id.toString(),
-          label: user.name || user.email,
-        };
-      });
-    }, [props.availableUsers]);
+  // Get available users for a role (excluding already assigned users for that role)
+  const getAvailableUsersForRole: (roleId: ObjectID) => Array<DropdownOption> =
+    useCallback(
+      (roleId: ObjectID): Array<DropdownOption> => {
+        const assignedUserIds: Set<string> = new Set(
+          getMembersForRole(roleId).map((m: AssignedMember) => {
+            return m.userId.toString();
+          }),
+        );
+        return props.availableUsers
+          .filter((user: AvailableUser) => {
+            return !assignedUserIds.has(user.id.toString());
+          })
+          .map((user: AvailableUser) => {
+            return {
+              value: user.id.toString(),
+              label: user.name || user.email,
+            };
+          });
+      },
+      [props.availableUsers, getMembersForRole],
+    );
 
   const cardTitle: string = props.title || "Team Members";
   const cardDescription: string =
@@ -159,6 +171,65 @@ const MemberRoleAssignment: FunctionComponent<ComponentProps> = (
     );
   }
 
+  // Render a single member row
+  const renderMemberRow: (
+    member: AssignedMember,
+    isLastInGroup?: boolean,
+  ) => ReactElement = (
+    member: AssignedMember,
+    isLastInGroup?: boolean,
+  ): ReactElement => {
+    return (
+      <div
+        key={member.memberId.toString()}
+        className={`flex items-center justify-between py-2 ${!isLastInGroup ? "border-b border-gray-100" : ""}`}
+      >
+        <div className="flex items-center gap-3">
+          {member.userProfilePictureUrl ? (
+            <Image
+              imageUrl={Route.fromString(member.userProfilePictureUrl)}
+              alt={member.userName}
+              className="h-8 w-8 rounded-full object-cover"
+            />
+          ) : (
+            <div className="h-8 w-8 rounded-full bg-gradient-to-br from-indigo-500 to-purple-600 flex items-center justify-center">
+              <span className="text-xs font-medium text-white">
+                {member.userName?.charAt(0)?.toUpperCase() ||
+                  member.userEmail?.charAt(0)?.toUpperCase() ||
+                  "?"}
+              </span>
+            </div>
+          )}
+          <div className="min-w-0">
+            <p className="text-sm font-medium text-gray-900 truncate">
+              {member.userName || member.userEmail}
+            </p>
+            {member.userName && member.userEmail && (
+              <p className="text-xs text-gray-500 truncate">
+                {member.userEmail}
+              </p>
+            )}
+          </div>
+        </div>
+        <button
+          type="button"
+          onClick={() => {
+            setShowConfirmDelete(member);
+          }}
+          disabled={isUnassigning?.toString() === member.memberId.toString()}
+          className="inline-flex items-center p-1.5 text-gray-400 hover:text-red-600 hover:bg-red-50 rounded-md transition-colors disabled:opacity-50"
+          title="Remove"
+        >
+          {isUnassigning?.toString() === member.memberId.toString() ? (
+            <Icon icon={IconProp.Refresh} className="w-4 h-4 animate-spin" />
+          ) : (
+            <Icon icon={IconProp.Close} className="w-4 h-4" />
+          )}
+        </button>
+      </div>
+    );
+  };
+
   return (
     <>
       <Card
@@ -202,232 +273,180 @@ const MemberRoleAssignment: FunctionComponent<ComponentProps> = (
               </p>
             </div>
           ) : (
-            <div className="overflow-hidden border border-gray-200 rounded-lg">
-              <table className="min-w-full divide-y divide-gray-200">
-                <thead className="bg-gray-50">
-                  <tr>
-                    <th
-                      scope="col"
-                      className="px-4 py-3 text-left text-xs font-semibold text-gray-600 uppercase tracking-wider w-1/3"
-                    >
-                      Role
-                    </th>
-                    <th
-                      scope="col"
-                      className="px-4 py-3 text-left text-xs font-semibold text-gray-600 uppercase tracking-wider"
-                    >
-                      Assigned Member
-                    </th>
-                    <th
-                      scope="col"
-                      className="px-4 py-3 text-right text-xs font-semibold text-gray-600 uppercase tracking-wider w-24"
-                    >
-                      Action
-                    </th>
-                  </tr>
-                </thead>
-                <tbody className="bg-white divide-y divide-gray-200">
-                  {props.roles.map((role: MemberRole) => {
-                    const member: AssignedMember | null = getMemberForRole(
-                      role.id,
-                    );
-                    const isDropdownActive: boolean =
-                      activeRoleDropdown?.toString() === role.id.toString();
-                    const availableUsers: Array<DropdownOption> =
-                      getUserDropdownOptions();
+            <div className="space-y-4">
+              {props.roles.map((role: MemberRole) => {
+                const members: Array<AssignedMember> = getMembersForRole(
+                  role.id,
+                );
+                const isDropdownActive: boolean =
+                  activeRoleDropdown?.toString() === role.id.toString();
+                const availableUsers: Array<DropdownOption> =
+                  getAvailableUsersForRole(role.id);
+                const canAddMore: boolean =
+                  role.canAssignMultipleUsers || members.length === 0;
 
-                    return (
-                      <tr key={role.id.toString()} className="hover:bg-gray-50">
-                        {/* Role Column */}
-                        <td className="px-4 py-4">
-                          <div className="flex items-center gap-3">
-                            <div
-                              className="w-8 h-8 rounded-lg flex items-center justify-center flex-shrink-0"
-                              style={{
-                                backgroundColor: role.color
-                                  ? `${role.color.toString()}20`
-                                  : "#f3f4f6",
-                              }}
-                            >
-                              <Icon
-                                icon={role.icon || IconProp.User}
-                                className="w-4 h-4"
-                                style={{
-                                  color: role.color?.toString() || "#6b7280",
-                                }}
-                              />
-                            </div>
-                            <div className="flex items-center gap-2">
-                              <span className="text-sm font-medium text-gray-900">
-                                {role.name}
-                              </span>
-                              {role.isPrimaryRole && (
-                                <span className="inline-flex items-center px-1.5 py-0.5 rounded text-xs font-medium bg-amber-100 text-amber-800">
-                                  Primary
-                                </span>
-                              )}
-                            </div>
-                          </div>
-                        </td>
-
-                        {/* Member Column */}
-                        <td className="px-4 py-4">
-                          {isDropdownActive ? (
-                            <div className="flex items-center gap-2">
-                              <div className="flex-1 max-w-xs">
-                                <Dropdown
-                                  options={availableUsers}
-                                  placeholder="Select member..."
-                                  onChange={(
-                                    value:
-                                      | DropdownValue
-                                      | Array<DropdownValue>
-                                      | null,
-                                  ) => {
-                                    if (value && !Array.isArray(value)) {
-                                      const option:
-                                        | DropdownOption
-                                        | undefined = availableUsers.find(
-                                        (opt: DropdownOption) => {
-                                          return (
-                                            opt.value.toString() ===
-                                            value.toString()
-                                          );
-                                        },
-                                      );
-                                      setSelectedUserOption(option || null);
-                                    } else {
-                                      setSelectedUserOption(null);
-                                    }
-                                  }}
-                                  value={selectedUserOption || undefined}
-                                />
-                              </div>
-                              <button
-                                type="button"
-                                onClick={() => {
-                                  if (selectedUserOption) {
-                                    handleAssign(
-                                      new ObjectID(
-                                        selectedUserOption.value.toString(),
-                                      ),
-                                      role.id,
-                                    );
-                                  }
-                                }}
-                                disabled={!selectedUserOption || isAssigning}
-                                className="inline-flex items-center px-3 py-1.5 text-xs font-medium text-white bg-indigo-600 border border-transparent rounded-md hover:bg-indigo-700 disabled:opacity-50 disabled:cursor-not-allowed transition-colors"
-                              >
-                                {isAssigning ? (
-                                  <Icon
-                                    icon={IconProp.Refresh}
-                                    className="w-3.5 h-3.5 animate-spin"
-                                  />
-                                ) : (
-                                  "Save"
-                                )}
-                              </button>
-                              <button
-                                type="button"
-                                onClick={() => {
-                                  setActiveRoleDropdown(null);
-                                  setSelectedUserOption(null);
-                                }}
-                                className="inline-flex items-center px-3 py-1.5 text-xs font-medium text-gray-600 bg-white border border-gray-300 rounded-md hover:bg-gray-50 transition-colors"
-                              >
-                                Cancel
-                              </button>
-                            </div>
-                          ) : member ? (
-                            <div className="flex items-center gap-3">
-                              {/* Avatar */}
-                              {member.userProfilePictureUrl ? (
-                                <Image
-                                  imageUrl={Route.fromString(
-                                    member.userProfilePictureUrl,
-                                  )}
-                                  alt={member.userName}
-                                  className="h-8 w-8 rounded-full object-cover"
-                                />
-                              ) : (
-                                <div className="h-8 w-8 rounded-full bg-gradient-to-br from-indigo-500 to-purple-600 flex items-center justify-center">
-                                  <span className="text-xs font-medium text-white">
-                                    {member.userName?.charAt(0)?.toUpperCase() ||
-                                      member.userEmail
-                                        ?.charAt(0)
-                                        ?.toUpperCase() ||
-                                      "?"}
-                                  </span>
-                                </div>
-                              )}
-                              {/* User Info */}
-                              <div className="min-w-0">
-                                <p className="text-sm font-medium text-gray-900 truncate">
-                                  {member.userName || member.userEmail}
-                                </p>
-                                {member.userName && member.userEmail && (
-                                  <p className="text-xs text-gray-500 truncate">
-                                    {member.userEmail}
-                                  </p>
-                                )}
-                              </div>
-                            </div>
-                          ) : (
-                            <span className="text-sm text-gray-400 italic">
-                              Not assigned
+                return (
+                  <div
+                    key={role.id.toString()}
+                    className="border border-gray-200 rounded-lg overflow-hidden"
+                  >
+                    {/* Role Header */}
+                    <div
+                      className="px-4 py-3 flex items-center justify-between"
+                      style={{
+                        backgroundColor: role.color
+                          ? `${role.color.toString()}10`
+                          : "#f9fafb",
+                      }}
+                    >
+                      <div className="flex items-center gap-3">
+                        <div
+                          className="w-9 h-9 rounded-lg flex items-center justify-center flex-shrink-0"
+                          style={{
+                            backgroundColor: role.color
+                              ? `${role.color.toString()}25`
+                              : "#e5e7eb",
+                          }}
+                        >
+                          <Icon
+                            icon={role.icon || IconProp.User}
+                            className="w-4.5 h-4.5"
+                            style={{
+                              color: role.color?.toString() || "#6b7280",
+                            }}
+                          />
+                        </div>
+                        <div>
+                          <div className="flex items-center gap-2">
+                            <span className="text-sm font-semibold text-gray-900">
+                              {role.name}
                             </span>
-                          )}
-                        </td>
+                            {role.isPrimaryRole && (
+                              <span className="inline-flex items-center px-1.5 py-0.5 rounded text-xs font-medium bg-amber-100 text-amber-800">
+                                Primary
+                              </span>
+                            )}
+                            {role.canAssignMultipleUsers && (
+                              <span className="inline-flex items-center px-1.5 py-0.5 rounded text-xs font-medium bg-blue-100 text-blue-700">
+                                Multiple
+                              </span>
+                            )}
+                          </div>
+                          <p className="text-xs text-gray-500 mt-0.5">
+                            {members.length}{" "}
+                            {members.length === 1 ? "member" : "members"}{" "}
+                            assigned
+                          </p>
+                        </div>
+                      </div>
 
-                        {/* Action Column */}
-                        <td className="px-4 py-4 text-right">
-                          {!isDropdownActive && (
-                            <>
-                              {member ? (
-                                <button
-                                  type="button"
-                                  onClick={() => {
-                                    setShowConfirmDelete(member);
-                                  }}
-                                  disabled={
-                                    isUnassigning?.toString() ===
-                                    member.memberId.toString()
-                                  }
-                                  className="inline-flex items-center px-2.5 py-1.5 text-xs font-medium text-red-600 bg-red-50 border border-red-200 rounded-md hover:bg-red-100 hover:border-red-300 transition-colors disabled:opacity-50"
-                                >
-                                  {isUnassigning?.toString() ===
-                                  member.memberId.toString() ? (
-                                    <Icon
-                                      icon={IconProp.Refresh}
-                                      className="w-3.5 h-3.5 animate-spin"
-                                    />
-                                  ) : (
-                                    "Remove"
-                                  )}
-                                </button>
-                              ) : availableUsers.length > 0 ? (
-                                <button
-                                  type="button"
-                                  onClick={() => {
-                                    setActiveRoleDropdown(role.id);
-                                  }}
-                                  className="inline-flex items-center px-2.5 py-1.5 text-xs font-medium text-indigo-600 bg-indigo-50 border border-indigo-200 rounded-md hover:bg-indigo-100 hover:border-indigo-300 transition-colors"
-                                >
-                                  Assign
-                                </button>
-                              ) : (
-                                <span className="text-xs text-gray-400">
-                                  No users
-                                </span>
-                              )}
-                            </>
-                          )}
-                        </td>
-                      </tr>
-                    );
-                  })}
-                </tbody>
-              </table>
+                      {/* Add Button */}
+                      {!isDropdownActive &&
+                        canAddMore &&
+                        availableUsers.length > 0 && (
+                          <button
+                            type="button"
+                            onClick={() => {
+                              setActiveRoleDropdown(role.id);
+                            }}
+                            className="inline-flex items-center gap-1.5 px-3 py-1.5 text-xs font-medium text-gray-700 bg-white border border-gray-300 rounded-md hover:bg-gray-50 hover:border-gray-400 transition-all shadow-sm"
+                          >
+                            <Icon icon={IconProp.Add} className="w-3.5 h-3.5" />
+                            {members.length === 0 ? "Assign" : "Add"}
+                          </button>
+                        )}
+                    </div>
+
+                    {/* Dropdown for adding member */}
+                    {isDropdownActive && (
+                      <div className="px-4 py-3 bg-gray-50 border-b border-gray-200">
+                        <div className="flex items-center gap-2">
+                          <div className="flex-1 max-w-sm">
+                            <Dropdown
+                              options={availableUsers}
+                              placeholder="Select member..."
+                              onChange={(
+                                value:
+                                  | DropdownValue
+                                  | Array<DropdownValue>
+                                  | null,
+                              ) => {
+                                if (value && !Array.isArray(value)) {
+                                  const option: DropdownOption | undefined =
+                                    availableUsers.find(
+                                      (opt: DropdownOption) => {
+                                        return (
+                                          opt.value.toString() ===
+                                          value.toString()
+                                        );
+                                      },
+                                    );
+                                  setSelectedUserOption(option || null);
+                                } else {
+                                  setSelectedUserOption(null);
+                                }
+                              }}
+                              value={selectedUserOption || undefined}
+                            />
+                          </div>
+                          <button
+                            type="button"
+                            onClick={() => {
+                              if (selectedUserOption) {
+                                handleAssign(
+                                  new ObjectID(
+                                    selectedUserOption.value.toString(),
+                                  ),
+                                  role.id,
+                                );
+                              }
+                            }}
+                            disabled={!selectedUserOption || isAssigning}
+                            className="inline-flex items-center px-3 py-1.5 text-xs font-medium text-white bg-indigo-600 border border-transparent rounded-md hover:bg-indigo-700 disabled:opacity-50 disabled:cursor-not-allowed transition-colors"
+                          >
+                            {isAssigning ? (
+                              <Icon
+                                icon={IconProp.Refresh}
+                                className="w-3.5 h-3.5 animate-spin"
+                              />
+                            ) : (
+                              "Save"
+                            )}
+                          </button>
+                          <button
+                            type="button"
+                            onClick={() => {
+                              setActiveRoleDropdown(null);
+                              setSelectedUserOption(null);
+                            }}
+                            className="inline-flex items-center px-3 py-1.5 text-xs font-medium text-gray-600 bg-white border border-gray-300 rounded-md hover:bg-gray-50 transition-colors"
+                          >
+                            Cancel
+                          </button>
+                        </div>
+                      </div>
+                    )}
+
+                    {/* Members List */}
+                    <div className="px-4 py-2 bg-white">
+                      {members.length === 0 ? (
+                        <p className="text-sm text-gray-400 italic py-2">
+                          Not assigned
+                        </p>
+                      ) : (
+                        members.map(
+                          (member: AssignedMember, index: number) => {
+                            return renderMemberRow(
+                              member,
+                              index === members.length - 1,
+                            );
+                          },
+                        )
+                      )}
+                    </div>
+                  </div>
+                );
+              })}
             </div>
           )}
         </div>
diff --git a/Dashboard/src/Components/Incident/IncidentMemberRoleAssignment.tsx b/Dashboard/src/Components/Incident/IncidentMemberRoleAssignment.tsx
index ed20e08ade..d3ddc6de15 100644
--- a/Dashboard/src/Components/Incident/IncidentMemberRoleAssignment.tsx
+++ b/Dashboard/src/Components/Incident/IncidentMemberRoleAssignment.tsx
@@ -70,6 +70,7 @@ const IncidentMemberRoleAssignment: FunctionComponent<ComponentProps> = (
               color: true,
               isPrimaryRole: true,
               roleIcon: true,
+              canAssignMultipleUsers: true,
             },
             sort: {
               isPrimaryRole: SortOrder.Descending,
@@ -118,6 +119,7 @@ const IncidentMemberRoleAssignment: FunctionComponent<ComponentProps> = (
             color: role.color || Color.fromString("#6b7280"),
             isPrimaryRole: role.isPrimaryRole || false,
             icon: role.roleIcon || undefined,
+            canAssignMultipleUsers: role.canAssignMultipleUsers || false,
           };
         });
 
diff --git a/Worker/DataMigrations/Index.ts b/Worker/DataMigrations/Index.ts
index 7714b33dd4..4efa279999 100644
--- a/Worker/DataMigrations/Index.ts
+++ b/Worker/DataMigrations/Index.ts
@@ -55,6 +55,7 @@ import LowercaseDomains from "./LowercaseDomains";
 import AddAttributeKeysColumnToTelemetryTables from "./AddAttributeKeysColumnToTelemetryTables";
 import AddDefaultIncidentRolesToExistingProjects from "./AddDefaultIncidentRolesToExistingProjects";
 import AddDefaultIconsToIncidentRoles from "./AddDefaultIconsToIncidentRoles";
+import UpdateObserverRoleToAllowMultipleUsers from "./UpdateObserverRoleToAllowMultipleUsers";
 
 // This is the order in which the migrations will be run. Add new migrations to the end of the array.
 
@@ -114,6 +115,7 @@ const DataMigrations: Array<DataMigrationBase> = [
   new AddAttributeKeysColumnToTelemetryTables(),
   new AddDefaultIncidentRolesToExistingProjects(),
   new AddDefaultIconsToIncidentRoles(),
+  new UpdateObserverRoleToAllowMultipleUsers(),
 ];
 
 export default DataMigrations;
diff --git a/Worker/DataMigrations/UpdateObserverRoleToAllowMultipleUsers.ts b/Worker/DataMigrations/UpdateObserverRoleToAllowMultipleUsers.ts
new file mode 100644
index 0000000000..096b4c612b
--- /dev/null
+++ b/Worker/DataMigrations/UpdateObserverRoleToAllowMultipleUsers.ts
@@ -0,0 +1,49 @@
+import DataMigrationBase from "./DataMigrationBase";
+import { LIMIT_INFINITY } from "Common/Types/Database/LimitMax";
+import IncidentRoleService from "Common/Server/Services/IncidentRoleService";
+import IncidentRole from "Common/Models/DatabaseModels/IncidentRole";
+
+export default class UpdateObserverRoleToAllowMultipleUsers extends DataMigrationBase {
+  public constructor() {
+    super("UpdateObserverRoleToAllowMultipleUsers");
+  }
+
+  public override async migrate(): Promise<void> {
+    // Get all Observer roles across all projects
+    const observerRoles: Array<IncidentRole> = await IncidentRoleService.findBy(
+      {
+        query: {
+          name: "Observer",
+        },
+        select: {
+          _id: true,
+          canAssignMultipleUsers: true,
+        },
+        skip: 0,
+        limit: LIMIT_INFINITY,
+        props: {
+          isRoot: true,
+        },
+      },
+    );
+
+    for (const role of observerRoles) {
+      // Update the role to allow multiple users
+      if (!role.canAssignMultipleUsers) {
+        await IncidentRoleService.updateOneById({
+          id: role.id!,
+          data: {
+            canAssignMultipleUsers: true,
+          },
+          props: {
+            isRoot: true,
+          },
+        });
+      }
+    }
+  }
+
+  public override async rollback(): Promise<void> {
+    return;
+  }
+}