diff --git a/lib/algora/bounties/bounties.ex b/lib/algora/bounties/bounties.ex
index 35f3a97bc..806ee0161 100644
--- a/lib/algora/bounties/bounties.ex
+++ b/lib/algora/bounties/bounties.ex
@@ -917,12 +917,14 @@ defmodule Algora.Bounties do
     |> join(:left, [t: t], r in assoc(t, :repository), as: :r)
     |> join(:left, [r: r], ro in assoc(r, :user), as: :ro)
     |> where([b], not is_nil(b.amount))
+    |> where([b], b.status != :cancelled)
     |> apply_criteria(criteria)
     |> order_by([b], desc: b.amount, desc: b.inserted_at, desc: b.id)
     |> select([b, o: o, t: t, ro: ro, r: r], %{
       id: b.id,
       inserted_at: b.inserted_at,
       amount: b.amount,
+      status: b.status,
       owner: %{
         id: o.id,
         name: o.name,
@@ -956,6 +958,7 @@ defmodule Algora.Bounties do
         join: user in assoc(c, :user),
         left_join: s in assoc(c, :source),
         where: t.id in ^ticket_ids,
+        where: c.status != :cancelled,
         select_merge: %{user: user, source: s}
     )
   end
diff --git a/lib/algora_web/controllers/webhooks/github_controller.ex b/lib/algora_web/controllers/webhooks/github_controller.ex
index 43bc6f8fc..b81ffe47f 100644
--- a/lib/algora_web/controllers/webhooks/github_controller.ex
+++ b/lib/algora_web/controllers/webhooks/github_controller.ex
@@ -71,6 +71,7 @@ defmodule AlgoraWeb.Webhooks.GithubController do
                from c in Claim,
                  join: s in assoc(c, :source),
                  join: u in assoc(c, :user),
+                 where: c.status != :cancelled,
                  where: s.id == ^source.id,
                  where: u.provider == "github",
                  where: u.provider_id == ^to_string(payload["pull_request"]["user"]["id"]),
@@ -82,7 +83,7 @@ defmodule AlgoraWeb.Webhooks.GithubController do
 
           %Claim{group_id: group_id} ->
             Repo.update_all(
-              from(c in Claim, where: c.group_id == ^group_id),
+              from(c in Claim, where: c.group_id == ^group_id, where: c.status != :cancelled),
               set: [status: :approved]
             )
 
@@ -93,6 +94,7 @@ defmodule AlgoraWeb.Webhooks.GithubController do
                 join: tru in assoc(tr, :user),
                 join: u in assoc(c, :user),
                 where: c.group_id == ^group_id,
+                where: c.status != :cancelled,
                 order_by: [desc: c.group_share, asc: c.inserted_at],
                 select_merge: %{
                   target: %{t | repository: %{tr | user: tru}},
diff --git a/test/algora/bounties_test.exs b/test/algora/bounties_test.exs
index 75698ba64..99d18bdd9 100644
--- a/test/algora/bounties_test.exs
+++ b/test/algora/bounties_test.exs
@@ -14,6 +14,14 @@ defmodule Algora.BountiesTest do
   alias Algora.PSP
   alias Bounties.Tip
 
+  setup do
+    repo_owner = insert!(:user)
+    repo = insert!(:repository, %{user: repo_owner})
+    ticket = insert!(:ticket, %{repository: repo})
+
+    %{ticket: ticket}
+  end
+
   describe "bounties" do
     test "create" do
       creator = insert!(:user)
@@ -369,4 +377,30 @@ defmodule Algora.BountiesTest do
       assert response == String.trim(expected_response)
     end
   end
+
+  describe "list_bounties/1" do
+    test "does not include cancelled bounties", %{ticket: ticket} do
+      insert!(:bounty, status: :open, ticket: ticket, owner: insert!(:user))
+      insert!(:bounty, status: :paid, ticket: ticket, owner: insert!(:user))
+      insert!(:bounty, status: :cancelled, ticket: ticket, owner: insert!(:user))
+
+      bounties = Bounties.list_bounties()
+      assert Enum.any?(bounties, &(&1.status == :open))
+      assert Enum.any?(bounties, &(&1.status == :paid))
+      refute Enum.any?(bounties, &(&1.status == :cancelled))
+    end
+  end
+
+  describe "list_claims/1" do
+    test "does not include cancelled claims", %{ticket: ticket} do
+      insert!(:claim, status: :pending, target: ticket, user: insert!(:user))
+      insert!(:claim, status: :approved, target: ticket, user: insert!(:user))
+      insert!(:claim, status: :cancelled, target: ticket, user: insert!(:user))
+
+      claims = Bounties.list_claims([ticket.id])
+      assert Enum.any?(claims, &(&1.status == :pending))
+      assert Enum.any?(claims, &(&1.status == :approved))
+      refute Enum.any?(claims, &(&1.status == :cancelled))
+    end
+  end
 end
diff --git a/test/algora_web/controllers/webhooks/github_controller_test.exs b/test/algora_web/controllers/webhooks/github_controller_test.exs
index 4b1a84019..ff211ee79 100644
--- a/test/algora_web/controllers/webhooks/github_controller_test.exs
+++ b/test/algora_web/controllers/webhooks/github_controller_test.exs
@@ -14,6 +14,7 @@ defmodule AlgoraWeb.Webhooks.GithubControllerTest do
   alias Algora.Github.Webhook
   alias Algora.Payments.Transaction
   alias Algora.Repo
+  alias Algora.Workspace.Ticket
   alias AlgoraWeb.Webhooks.GithubController
 
   setup do
@@ -220,7 +221,7 @@ defmodule AlgoraWeb.Webhooks.GithubControllerTest do
 
     test "does not allow multiple claims in a single PR", ctx do
       issue_number1 = :rand.uniform(1000)
-      issue_number2 = :rand.uniform(1000)
+      issue_number2 = issue_number1 + 1
       pr_number = :rand.uniform(1000)
 
       process_scenario!(ctx, [
@@ -252,7 +253,7 @@ defmodule AlgoraWeb.Webhooks.GithubControllerTest do
 
     test "cancels existing claim when attempting to claim a different bounty in the same PR", ctx do
       issue_number1 = :rand.uniform(1000)
-      issue_number2 = :rand.uniform(1000)
+      issue_number2 = issue_number1 + 1
       pr_number = :rand.uniform(1000)
 
       process_scenario!(ctx, [
@@ -510,6 +511,79 @@ defmodule AlgoraWeb.Webhooks.GithubControllerTest do
       assert is_nil(transfer)
     end
 
+    test "handles autopay when claim is changed to a different bounty and PR is merged", ctx do
+      issue_number1 = :rand.uniform(1000)
+      issue_number2 = issue_number1 + :rand.uniform(1000)
+      pr_number = issue_number1 + :rand.uniform(1000)
+
+      customer = insert!(:customer, user: ctx[:org])
+      _payment_method = insert!(:payment_method, is_default: true, customer: customer)
+
+      process_scenario!(ctx, [
+        %{
+          event_action: "issue_comment.created",
+          user_type: :admin,
+          body: "/bounty $100",
+          params: %{"issue" => %{"number" => issue_number1}}
+        },
+        %{
+          event_action: "issue_comment.created",
+          user_type: :admin,
+          body: "/bounty $200",
+          params: %{"issue" => %{"number" => issue_number2}}
+        },
+        %{
+          event_action: "pull_request.opened",
+          user_type: :unauthorized,
+          body: "/claim #{issue_number1}",
+          params: %{"pull_request" => %{"number" => pr_number}}
+        },
+        %{
+          event_action: "pull_request.edited",
+          user_type: :unauthorized,
+          body: "/claim #{issue_number2}",
+          params: %{"pull_request" => %{"number" => pr_number}}
+        },
+        %{
+          event_action: "pull_request.closed",
+          user_type: :unauthorized,
+          body: "/claim #{issue_number2}",
+          params: %{"pull_request" => %{"number" => pr_number, "merged_at" => DateTime.to_iso8601(DateTime.utc_now())}}
+        }
+      ])
+
+      ticket1 = Repo.get_by!(Ticket, number: issue_number1)
+      ticket2 = Repo.get_by!(Ticket, number: issue_number2)
+
+      _bounty1 = Repo.get_by!(Bounty, ticket_id: ticket1.id)
+      bounty2 = Repo.get_by!(Bounty, ticket_id: ticket2.id)
+
+      cancelled_claim = Repo.get_by!(Claim, target_id: ticket1.id)
+      active_claim = Repo.get_by!(Claim, target_id: ticket2.id)
+
+      assert active_claim.status == :approved
+      assert cancelled_claim.status == :cancelled
+
+      charge = Repo.one!(from t in Transaction, where: t.type == :charge)
+      assert Money.equal?(charge.net_amount, Money.new(:USD, 200))
+      assert charge.status == :initialized
+      assert charge.user_id == ctx[:org].id
+
+      debit = Repo.one!(from t in Transaction, where: t.type == :debit)
+      assert Money.equal?(debit.net_amount, Money.new(:USD, 200))
+      assert debit.status == :initialized
+      assert debit.user_id == ctx[:org].id
+      assert debit.bounty_id == bounty2.id
+      assert debit.claim_id == active_claim.id
+
+      credit = Repo.one!(from t in Transaction, where: t.type == :credit)
+      assert Money.equal?(credit.net_amount, Money.new(:USD, 200))
+      assert credit.status == :initialized
+      assert credit.user_id == ctx[:unauthorized_user].id
+      assert credit.bounty_id == bounty2.id
+      assert credit.claim_id == active_claim.id
+    end
+
     test "prevents duplicate transaction creation when receiving multiple PR closed events", ctx do
       issue_number = :rand.uniform(1000)
       pr_number = :rand.uniform(1000)
diff --git a/test/support/factory.ex b/test/support/factory.ex
index 08a036193..dadfca06b 100644
--- a/test/support/factory.ex
+++ b/test/support/factory.ex
@@ -202,7 +202,9 @@ defmodule Algora.Factory do
 
   def bounty_factory do
     %Algora.Bounties.Bounty{
-      id: Nanoid.generate()
+      id: Nanoid.generate(),
+      status: :open,
+      amount: Money.new!(100, :USD)
     }
   end