diff --git a/token/invocation/invocation_test.go b/token/invocation/invocation_test.go
index eb15889..b103869 100644
--- a/token/invocation/invocation_test.go
+++ b/token/invocation/invocation_test.go
@@ -197,7 +197,7 @@ func TestToken_ExecutionAllowed(t *testing.T) {
 			cmd:    delegationtest.NominalCommand,
 			args:   emptyArguments,
 			proofs: []cid.Cid{delegationtest.TokenBobBobCID},
-			err:    invocation.ErrBrokenChain,
+			err:    invocation.ErrWrongSub,
 		},
 	} {
 		t.Run(tc.name, func(t *testing.T) {
@@ -206,6 +206,8 @@ func TestToken_ExecutionAllowed(t *testing.T) {
 			tkn, err := invocation.New(tc.issuer.DID(), tc.cmd, didtest.PersonaAlice.DID(), tc.proofs, tc.opts...)
 			require.NoError(t, err)
 
+			t.Log(tkn.String())
+
 			err = tkn.ExecutionAllowed(delegationtest.GetDelegationLoader())
 
 			if tc.err != nil {
diff --git a/toolkit/client/proof.go b/toolkit/client/proof.go
index 14d557d..5bcf562 100644
--- a/toolkit/client/proof.go
+++ b/toolkit/client/proof.go
@@ -21,8 +21,7 @@ import (
 // Note: the returned delegation(s) don't have to match exactly the parameters, as long as they allow them.
 // Note: the implemented algorithm won't perform well with a large number of delegations.
 func FindProof(dlgs func() iter.Seq[*delegation.Bundle], issuer did.DID, cmd command.Command, subject did.DID) []cid.Cid {
-	// TODO: maybe that should be part of delegation.Token directly?
-	dlgMatch := func(dlg *delegation.Token, issuer did.DID, cmd command.Command, subject did.DID) bool {
+	continuePath := func(dlg *delegation.Token, issuer did.DID, cmd command.Command, subject did.DID) bool {
 		// The Subject of each delegation must equal the invocation's Subject (or Audience if defined). - 4f
 		if !dlg.Subject().Equal(subject) {
 			return false
@@ -47,7 +46,7 @@ func FindProof(dlgs func() iter.Seq[*delegation.Bundle], issuer did.DID, cmd com
 	var candidateLeaf []*delegation.Bundle
 
 	for bundle := range dlgs() {
-		if !dlgMatch(bundle.Decoded, issuer, cmd, subject) {
+		if !continuePath(bundle.Decoded, issuer, cmd, subject) {
 			continue
 		}
 		candidateLeaf = append(candidateLeaf, bundle)
@@ -83,7 +82,12 @@ func FindProof(dlgs func() iter.Seq[*delegation.Bundle], issuer did.DID, cmd com
 
 			// find parent delegation for our current delegation
 			for candidate := range dlgs() {
-				if !dlgMatch(candidate.Decoded, at.Decoded.Issuer(), at.Decoded.Command(), subject) {
+				// Prune the delegations that don't match the current proof.
+				if !continuePath(candidate.Decoded, at.Decoded.Issuer(), at.Decoded.Command(), subject) {
+					continue
+				}
+				// Prune the self-delegations as they can't get us closer to what we are looking for.
+				if candidate.Decoded.Issuer().Equal(candidate.Decoded.Audience()) {
 					continue
 				}
 
diff --git a/toolkit/client/proof_test.go b/toolkit/client/proof_test.go
index c729418..403fae5 100644
--- a/toolkit/client/proof_test.go
+++ b/toolkit/client/proof_test.go
@@ -4,7 +4,9 @@ import (
 	"iter"
 	"testing"
 
+	"github.com/MetaMask/go-did-it"
 	"github.com/MetaMask/go-did-it/didtest"
+	"github.com/ipfs/go-cid"
 	"github.com/stretchr/testify/require"
 
 	"github.com/ucan-wg/go-ucan/pkg/command"
@@ -23,17 +25,76 @@ func TestFindProof(t *testing.T) {
 		}
 	}
 
-	require.Equal(t, delegationtest.ProofAliceBob,
-		FindProof(dlgs, didtest.PersonaBob.DID(), delegationtest.NominalCommand, didtest.PersonaAlice.DID()))
-	require.Equal(t, delegationtest.ProofAliceBobCarol,
-		FindProof(dlgs, didtest.PersonaCarol.DID(), delegationtest.NominalCommand, didtest.PersonaAlice.DID()))
-	require.Equal(t, delegationtest.ProofAliceBobCarolDan,
-		FindProof(dlgs, didtest.PersonaDan.DID(), delegationtest.NominalCommand, didtest.PersonaAlice.DID()))
-	require.Equal(t, delegationtest.ProofAliceBobCarolDanErin,
-		FindProof(dlgs, didtest.PersonaErin.DID(), delegationtest.NominalCommand, didtest.PersonaAlice.DID()))
-	require.Equal(t, delegationtest.ProofAliceBobCarolDanErinFrank,
-		FindProof(dlgs, didtest.PersonaFrank.DID(), delegationtest.NominalCommand, didtest.PersonaAlice.DID()))
+	for _, tc := range []struct {
+		name     string
+		issuer   did.DID
+		command  command.Command
+		subject  did.DID
+		expected []cid.Cid
+	}{
+		// Passes
+		{
+			name:     "Alice --> Alice (self-delegation)",
+			issuer:   didtest.PersonaAlice.DID(),
+			command:  delegationtest.NominalCommand,
+			subject:  didtest.PersonaAlice.DID(),
+			expected: []cid.Cid{delegationtest.TokenAliceAliceCID},
+		},
+		{
+			name:     "Alice --> Bob",
+			issuer:   didtest.PersonaBob.DID(),
+			command:  delegationtest.NominalCommand,
+			subject:  didtest.PersonaAlice.DID(),
+			expected: delegationtest.ProofAliceBob,
+		},
+		{
+			name:     "Alice --> Bob --> Carol",
+			issuer:   didtest.PersonaCarol.DID(),
+			command:  delegationtest.NominalCommand,
+			subject:  didtest.PersonaAlice.DID(),
+			expected: delegationtest.ProofAliceBobCarol,
+		},
+		{
+			name:     "Alice --> Bob --> Carol --> Dan",
+			issuer:   didtest.PersonaDan.DID(),
+			command:  delegationtest.NominalCommand,
+			subject:  didtest.PersonaAlice.DID(),
+			expected: delegationtest.ProofAliceBobCarolDan,
+		},
+		{
+			name:     "Alice --> Bob --> Carol --> Dan --> Erin",
+			issuer:   didtest.PersonaErin.DID(),
+			command:  delegationtest.NominalCommand,
+			subject:  didtest.PersonaAlice.DID(),
+			expected: delegationtest.ProofAliceBobCarolDanErin,
+		},
+		{
+			name:     "Alice --> Bob --> Carol --> Dan --> Erin --> Frank",
+			issuer:   didtest.PersonaFrank.DID(),
+			command:  delegationtest.NominalCommand,
+			subject:  didtest.PersonaAlice.DID(),
+			expected: delegationtest.ProofAliceBobCarolDanErinFrank,
+		},
 
-	// wrong command
-	require.Empty(t, FindProof(dlgs, didtest.PersonaBob.DID(), command.New("foo"), didtest.PersonaAlice.DID()))
+		// Fails
+		{
+			name:     "wrong command",
+			issuer:   didtest.PersonaBob.DID(),
+			command:  command.New("foo"),
+			subject:  didtest.PersonaAlice.DID(),
+			expected: nil,
+		},
+		{
+			name:     "wrong subject",
+			issuer:   didtest.PersonaBob.DID(),
+			command:  delegationtest.NominalCommand,
+			subject:  didtest.PersonaDan.DID(),
+			expected: nil,
+		},
+	} {
+		t.Run(tc.name, func(t *testing.T) {
+			res := FindProof(dlgs, tc.issuer, tc.command, tc.subject)
+			require.Equal(t, tc.expected, res)
+		})
+	}
 }