diff --git a/apps/remix/app/components/dialogs/team-delete-dialog.tsx b/apps/remix/app/components/dialogs/team-delete-dialog.tsx
index 670ba1a2a..ac735e1ff 100644
--- a/apps/remix/app/components/dialogs/team-delete-dialog.tsx
+++ b/apps/remix/app/components/dialogs/team-delete-dialog.tsx
@@ -8,6 +8,7 @@ import { useForm } from 'react-hook-form';
 import { useNavigate } from 'react-router';
 import { z } from 'zod';
 
+import { useCurrentOrganisation } from '@documenso/lib/client-only/providers/organisation';
 import { useSession } from '@documenso/lib/client-only/providers/session';
 import { AppError } from '@documenso/lib/errors/app-error';
 import { trpc } from '@documenso/trpc/react';
@@ -30,6 +31,13 @@ import {
   FormMessage,
 } from '@documenso/ui/primitives/form/form';
 import { Input } from '@documenso/ui/primitives/input';
+import {
+  Select,
+  SelectContent,
+  SelectItem,
+  SelectTrigger,
+  SelectValue,
+} from '@documenso/ui/primitives/select';
 import type { Toast } from '@documenso/ui/primitives/use-toast';
 import { useToast } from '@documenso/ui/primitives/use-toast';
 
@@ -53,26 +61,34 @@ export const TeamDeleteDialog = ({
   const { toast } = useToast();
   const { refreshSession } = useSession();
 
+  const currentOrganisation = useCurrentOrganisation();
+
   const deleteMessage = _(msg`delete ${teamName}`);
 
+  const filteredTeams = currentOrganisation.teams.filter((team) => team.id !== teamId);
+
   const ZDeleteTeamFormSchema = z.object({
     teamName: z.literal(deleteMessage, {
       errorMap: () => ({ message: _(msg`You must enter '${deleteMessage}' to proceed`) }),
     }),
+    transferTeamId: z.string().optional(),
   });
 
   const form = useForm({
     resolver: zodResolver(ZDeleteTeamFormSchema),
     defaultValues: {
       teamName: '',
+      transferTeamId: undefined,
     },
   });
 
   const { mutateAsync: deleteTeam } = trpc.team.delete.useMutation();
 
-  const onFormSubmit = async () => {
+  const onFormSubmit = async (data: z.infer<typeof ZDeleteTeamFormSchema>) => {
     try {
-      await deleteTeam({ teamId });
+      const transferTeamId = data.transferTeamId ? parseInt(data.transferTeamId, 10) : undefined;
+
+      await deleteTeam({ teamId, transferTeamId: transferTeamId || undefined });
 
       await refreshSession();
 
@@ -168,6 +184,43 @@ export const TeamDeleteDialog = ({
                 )}
               />
 
+              {filteredTeams.length > 0 && (
+                <FormField
+                  control={form.control}
+                  name="transferTeamId"
+                  render={({ field }) => (
+                    <FormItem>
+                      <FormLabel>
+                        <Trans>Transfer documents to a different team</Trans>
+                      </FormLabel>
+                      <FormControl>
+                        <Select {...field} onValueChange={field.onChange}>
+                          <SelectTrigger>
+                            <SelectValue
+                              placeholder={_(msg`Don't transfer (Delete all documents)`)}
+                            />
+                          </SelectTrigger>
+
+                          <SelectContent>
+                            <SelectItem value="-1">
+                              <Trans>Don't transfer (Delete all documents)</Trans>
+                            </SelectItem>
+
+                            {filteredTeams.map((team) => (
+                              <SelectItem key={team.id} value={team.id.toString()}>
+                                {team.name}
+                              </SelectItem>
+                            ))}
+                          </SelectContent>
+                        </Select>
+                      </FormControl>
+
+                      <FormMessage />
+                    </FormItem>
+                  )}
+                />
+              )}
+
               <DialogFooter>
                 <Button type="button" variant="secondary" onClick={() => setOpen(false)}>
                   <Trans>Cancel</Trans>
diff --git a/packages/lib/server-only/envelope/orphan-envelopes.ts b/packages/lib/server-only/envelope/orphan-envelopes.ts
new file mode 100644
index 000000000..75cf6ee88
--- /dev/null
+++ b/packages/lib/server-only/envelope/orphan-envelopes.ts
@@ -0,0 +1,52 @@
+import { DocumentStatus, EnvelopeType } from '@prisma/client';
+
+import { prisma } from '@documenso/prisma';
+
+import { deletedAccountServiceAccount } from '../user/service-accounts/deleted-account';
+
+export type OrphanEnvelopesOptions = {
+  teamId: number;
+};
+
+export const orphanEnvelopes = async ({ teamId }: OrphanEnvelopesOptions) => {
+  const serviceAccount = await deletedAccountServiceAccount();
+
+  // Transfer all inflight and completed envelopes to the service account.
+  await prisma.envelope.updateMany({
+    where: {
+      teamId,
+      type: EnvelopeType.DOCUMENT,
+      status: {
+        in: [DocumentStatus.PENDING, DocumentStatus.REJECTED, DocumentStatus.COMPLETED],
+      },
+      deletedAt: null,
+    },
+    data: {
+      userId: serviceAccount.id,
+      teamId: serviceAccount.ownedOrganisations[0].teams[0].id,
+      deletedAt: new Date(),
+    },
+  });
+
+  // Transfer any remaining deleted envelopes to the service account.
+  await prisma.envelope.updateMany({
+    where: {
+      teamId,
+      type: EnvelopeType.DOCUMENT,
+      status: {
+        in: [DocumentStatus.PENDING, DocumentStatus.REJECTED, DocumentStatus.COMPLETED],
+      },
+    },
+    data: {
+      userId: serviceAccount.id,
+      teamId: serviceAccount.ownedOrganisations[0].teams[0].id,
+    },
+  });
+
+  // Then delete anything remaining across documents and templates.
+  await prisma.envelope.deleteMany({
+    where: {
+      teamId,
+    },
+  });
+};
diff --git a/packages/lib/server-only/envelope/transfer-team-envelopes.ts b/packages/lib/server-only/envelope/transfer-team-envelopes.ts
new file mode 100644
index 000000000..944b14d43
--- /dev/null
+++ b/packages/lib/server-only/envelope/transfer-team-envelopes.ts
@@ -0,0 +1,20 @@
+import { prisma } from '@documenso/prisma';
+
+export type TransferTeamEnvelopesOptions = {
+  sourceTeamId: number;
+  targetTeamId: number;
+};
+
+export const transferTeamEnvelopes = async ({
+  sourceTeamId,
+  targetTeamId,
+}: TransferTeamEnvelopesOptions) => {
+  await prisma.envelope.updateMany({
+    where: {
+      teamId: sourceTeamId,
+    },
+    data: {
+      teamId: targetTeamId,
+    },
+  });
+};
diff --git a/packages/lib/server-only/user/delete-user.ts b/packages/lib/server-only/user/delete-user.ts
index ccc7f7476..6a4da06a2 100644
--- a/packages/lib/server-only/user/delete-user.ts
+++ b/packages/lib/server-only/user/delete-user.ts
@@ -1,9 +1,7 @@
-import { DocumentStatus, EnvelopeType } from '@prisma/client';
-
 import { prisma } from '@documenso/prisma';
 
 import { AppError, AppErrorCode } from '../../errors/app-error';
-import { deletedAccountServiceAccount } from './service-accounts/deleted-account';
+import { orphanEnvelopes } from '../envelope/orphan-envelopes';
 
 export type DeleteUserOptions = {
   id: number;
@@ -14,6 +12,30 @@ export const deleteUser = async ({ id }: DeleteUserOptions) => {
     where: {
       id,
     },
+    include: {
+      ownedOrganisations: {
+        include: {
+          teams: {
+            select: {
+              id: true,
+            },
+          },
+        },
+      },
+      organisationMember: {
+        include: {
+          organisation: {
+            include: {
+              teams: {
+                select: {
+                  id: true,
+                },
+              },
+            },
+          },
+        },
+      },
+    },
   });
 
   if (!user) {
@@ -22,22 +44,36 @@ export const deleteUser = async ({ id }: DeleteUserOptions) => {
     });
   }
 
-  const serviceAccount = await deletedAccountServiceAccount();
+  // Get team IDs from organisations the user owns.
+  const ownedTeamIds = user.ownedOrganisations.flatMap((org) => org.teams.map((team) => team.id));
 
-  // TODO: Send out cancellations for all pending docs
-  await prisma.envelope.updateMany({
-    where: {
-      userId: user.id,
-      type: EnvelopeType.DOCUMENT,
-      status: {
-        in: [DocumentStatus.PENDING, DocumentStatus.REJECTED, DocumentStatus.COMPLETED],
-      },
-    },
-    data: {
-      userId: serviceAccount.id,
-      deletedAt: new Date(),
-    },
-  });
+  // Get team IDs from organisations the user is a member of (but not owner).
+  const memberTeams = user.organisationMember
+    .filter((member) => member.organisation.ownerUserId !== user.id)
+    .flatMap((member) =>
+      member.organisation.teams.map((team) => ({
+        teamId: team.id,
+        orgOwnerId: member.organisation.ownerUserId,
+      })),
+    );
+
+  // For teams where user is the org owner - orphan their envelopes.
+  await Promise.all(ownedTeamIds.map(async (teamId) => orphanEnvelopes({ teamId })));
+
+  // For teams where user is a member (not owner) - transfer envelopes to team owner.
+  await Promise.all(
+    memberTeams.map(async ({ teamId, orgOwnerId }) => {
+      return prisma.envelope.updateMany({
+        where: {
+          userId: user.id,
+          teamId,
+        },
+        data: {
+          userId: orgOwnerId,
+        },
+      });
+    }),
+  );
 
   return await prisma.user.delete({
     where: {
diff --git a/packages/lib/server-only/user/service-accounts/deleted-account.ts b/packages/lib/server-only/user/service-accounts/deleted-account.ts
index 6bfd6d25f..2c54d2f8c 100644
--- a/packages/lib/server-only/user/service-accounts/deleted-account.ts
+++ b/packages/lib/server-only/user/service-accounts/deleted-account.ts
@@ -5,6 +5,20 @@ export const deletedAccountServiceAccount = async () => {
     where: {
       email: 'deleted-account@documenso.com',
     },
+    select: {
+      id: true,
+      email: true,
+      ownedOrganisations: {
+        select: {
+          id: true,
+          teams: {
+            select: {
+              id: true,
+            },
+          },
+        },
+      },
+    },
   });
 
   if (!serviceAccount) {
diff --git a/packages/trpc/server/organisation-router/delete-organisation.ts b/packages/trpc/server/organisation-router/delete-organisation.ts
index f20fede2d..b22a7c4d2 100644
--- a/packages/trpc/server/organisation-router/delete-organisation.ts
+++ b/packages/trpc/server/organisation-router/delete-organisation.ts
@@ -3,6 +3,7 @@ import {
   ORGANISATION_USER_ACCOUNT_TYPE,
 } from '@documenso/lib/constants/organisations';
 import { AppError, AppErrorCode } from '@documenso/lib/errors/app-error';
+import { orphanEnvelopes } from '@documenso/lib/server-only/envelope/orphan-envelopes';
 import { buildOrganisationWhereQuery } from '@documenso/lib/utils/organisations';
 import { prisma } from '@documenso/prisma';
 
@@ -32,6 +33,19 @@ export const deleteOrganisationRoute = authenticatedProcedure
         userId: user.id,
         roles: ORGANISATION_MEMBER_ROLE_PERMISSIONS_MAP['DELETE_ORGANISATION'],
       }),
+      select: {
+        id: true,
+        owner: {
+          select: {
+            id: true,
+          },
+        },
+        teams: {
+          select: {
+            id: true,
+          },
+        },
+      },
     });
 
     if (!organisation) {
@@ -40,6 +54,9 @@ export const deleteOrganisationRoute = authenticatedProcedure
       });
     }
 
+    // Orphan all envelopes to get rid of foreign key constraints.
+    await Promise.all(organisation.teams.map(async (team) => orphanEnvelopes({ teamId: team.id })));
+
     await prisma.$transaction(async (tx) => {
       await tx.account.deleteMany({
         where: {
diff --git a/packages/trpc/server/team-router/delete-team.ts b/packages/trpc/server/team-router/delete-team.ts
index 2624a902b..6f53f04c3 100644
--- a/packages/trpc/server/team-router/delete-team.ts
+++ b/packages/trpc/server/team-router/delete-team.ts
@@ -1,4 +1,10 @@
+import { TeamMemberRole } from '@prisma/client';
+
+import { AppError, AppErrorCode } from '@documenso/lib/errors/app-error';
+import { orphanEnvelopes } from '@documenso/lib/server-only/envelope/orphan-envelopes';
+import { transferTeamEnvelopes } from '@documenso/lib/server-only/envelope/transfer-team-envelopes';
 import { deleteTeam } from '@documenso/lib/server-only/team/delete-team';
+import { getTeamById } from '@documenso/lib/server-only/team/get-team';
 
 import { authenticatedProcedure } from '../trpc';
 import { ZDeleteTeamRequestSchema, ZDeleteTeamResponseSchema } from './delete-team.types';
@@ -8,15 +14,40 @@ export const deleteTeamRoute = authenticatedProcedure
   .input(ZDeleteTeamRequestSchema)
   .output(ZDeleteTeamResponseSchema)
   .mutation(async ({ input, ctx }) => {
-    const { teamId } = input;
+    const { teamId, transferTeamId } = input;
     const { user } = ctx;
 
+    const team = await getTeamById({ userId: user.id, teamId });
+
+    if (team.currentTeamRole !== TeamMemberRole.ADMIN) {
+      throw new AppError(AppErrorCode.UNAUTHORIZED, {
+        message: 'You are not allowed to delete this team',
+      });
+    }
+
     ctx.logger.info({
       input: {
         teamId,
       },
     });
 
+    const transferTeam = transferTeamId
+      ? await getTeamById({ userId: user.id, teamId: transferTeamId }).catch(() => {
+          throw new AppError(AppErrorCode.INVALID_REQUEST, {
+            message: 'Invalid transfer team ID',
+          });
+        })
+      : undefined;
+
+    if (transferTeam) {
+      await transferTeamEnvelopes({
+        sourceTeamId: teamId,
+        targetTeamId: transferTeam.id,
+      });
+    } else {
+      await orphanEnvelopes({ teamId });
+    }
+
     await deleteTeam({
       userId: user.id,
       teamId,
diff --git a/packages/trpc/server/team-router/delete-team.types.ts b/packages/trpc/server/team-router/delete-team.types.ts
index f4fe56545..4b5179d6f 100644
--- a/packages/trpc/server/team-router/delete-team.types.ts
+++ b/packages/trpc/server/team-router/delete-team.types.ts
@@ -12,6 +12,7 @@ import { z } from 'zod';
 
 export const ZDeleteTeamRequestSchema = z.object({
   teamId: z.number(),
+  transferTeamId: z.number().optional(),
 });
 
 export const ZDeleteTeamResponseSchema = z.void();