diff --git a/testing/internal/e2e/tests/base/paginate_session_test.go b/testing/internal/e2e/tests/base/paginate_session_test.go
new file mode 100644
index 0000000000..c7ee8e6888
--- /dev/null
+++ b/testing/internal/e2e/tests/base/paginate_session_test.go
@@ -0,0 +1,167 @@
+// Copyright (c) HashiCorp, Inc.
+// SPDX-License-Identifier: BUSL-1.1
+
+package base_test
+
+import (
+	"context"
+	"encoding/json"
+	"testing"
+
+	"github.com/hashicorp/boundary/api/scopes"
+	"github.com/hashicorp/boundary/api/sessions"
+	"github.com/hashicorp/boundary/api/targets"
+	"github.com/hashicorp/boundary/testing/internal/e2e"
+	"github.com/hashicorp/boundary/testing/internal/e2e/boundary"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+)
+
+// TestCliPaginateSessions asserts that the CLI automatically paginates to retrieve
+// all sessions in a single invocation. Canceling sessions is flaky so checking for
+// canceled sessions is not included.
+func TestCliPaginateSessions(t *testing.T) {
+	e2e.MaybeSkipTest(t)
+	c, err := loadTestConfig()
+	require.NoError(t, err)
+
+	ctx := context.Background()
+	boundary.AuthenticateAdminCli(t, ctx)
+	newOrgId := boundary.CreateNewOrgCli(t, ctx)
+	t.Cleanup(func() {
+		ctx := context.Background()
+		boundary.AuthenticateAdminCli(t, ctx)
+		output := e2e.RunCommand(ctx, "boundary", e2e.WithArgs("scopes", "delete", "-id", newOrgId))
+		require.NoError(t, output.Err, string(output.Stderr))
+	})
+
+	newProjectId := boundary.CreateNewProjectCli(t, ctx, newOrgId)
+	newHostCatalogId := boundary.CreateNewHostCatalogCli(t, ctx, newProjectId)
+	newHostSetId := boundary.CreateNewHostSetCli(t, ctx, newHostCatalogId)
+	newHostId := boundary.CreateNewHostCli(t, ctx, newHostCatalogId, c.TargetAddress)
+	boundary.AddHostToHostSetCli(t, ctx, newHostSetId, newHostId)
+	require.NoError(t, err)
+	newTargetId := boundary.CreateNewTargetCli(t, ctx, newProjectId, c.TargetPort)
+	boundary.AddHostSourceToTargetCli(t, ctx, newTargetId, newHostSetId)
+
+	// Connect to targets to create a session
+	// Create enough sessions to overflow a single page
+	for i := 0; i < c.MaxPageSize+1; i++ {
+		boundary.ConnectCli(t, ctx, newTargetId)
+	}
+
+	// List sessions recursively
+	output := e2e.RunCommand(ctx, "boundary",
+		e2e.WithArgs(
+			"sessions", "list",
+			"-scope-id", newProjectId,
+			"-format=json",
+		),
+	)
+	require.NoError(t, output.Err, string(output.Stderr))
+
+	var initialSessions sessions.SessionListResult
+	err = json.Unmarshal(output.Stdout, &initialSessions)
+	require.NoError(t, err)
+
+	require.Len(t, initialSessions.Items, c.MaxPageSize+1)
+	// Note that none of these are returned to the CLI for now.
+	assert.Empty(t, initialSessions.ResponseType)
+	assert.Empty(t, initialSessions.RemovedIds)
+	assert.Empty(t, initialSessions.ListToken)
+
+	// Create a new session
+	boundary.ConnectCli(t, ctx, newTargetId)
+
+	// List again, should have the new session
+	output = e2e.RunCommand(ctx, "boundary",
+		e2e.WithArgs(
+			"sessions", "list",
+			"-scope-id", newProjectId,
+			"-format=json",
+		),
+	)
+	require.NoError(t, output.Err, string(output.Stderr))
+
+	var newSessions sessions.SessionListResult
+	err = json.Unmarshal(output.Stdout, &newSessions)
+	require.NoError(t, err)
+
+	require.Len(t, newSessions.Items, c.MaxPageSize+2)
+	assert.Empty(t, newSessions.ResponseType)
+	assert.Empty(t, newSessions.RemovedIds)
+	assert.Empty(t, newSessions.ListToken)
+}
+
+// TestApiPaginateSessions asserts that the API automatically paginates to retrieve
+// all sessions in a single invocation. Canceling sessions is flaky so checking for
+// canceled sessions is not included.
+func TestApiPaginateSessions(t *testing.T) {
+	e2e.MaybeSkipTest(t)
+	c, err := loadTestConfig()
+	require.NoError(t, err)
+
+	client, err := boundary.NewApiClient()
+	require.NoError(t, err)
+	ctx := context.Background()
+	newOrgId := boundary.CreateNewOrgApi(t, ctx, client)
+	sClient := sessions.NewClient(client)
+	tClient := targets.NewClient(client)
+	t.Cleanup(func() {
+		ctx := context.Background()
+		scopeClient := scopes.NewClient(client)
+		_, err := scopeClient.Delete(ctx, newOrgId)
+		require.NoError(t, err)
+	})
+
+	newProjectId := boundary.CreateNewProjectApi(t, ctx, client, newOrgId)
+	newHostCatalogId := boundary.CreateNewHostCatalogApi(t, ctx, client, newProjectId)
+	newHostSetId := boundary.CreateNewHostSetApi(t, ctx, client, newHostCatalogId)
+	newHostId := boundary.CreateNewHostApi(t, ctx, client, newHostCatalogId, c.TargetAddress)
+	boundary.AddHostToHostSetApi(t, ctx, client, newHostSetId, newHostId)
+	require.NoError(t, err)
+	newTargetId := boundary.CreateNewTargetApi(t, ctx, client, newProjectId, c.TargetPort)
+	boundary.AddHostSourceToTargetApi(t, ctx, client, newTargetId, newHostSetId)
+
+	// Connect to targets to create a session
+	// Create enough sessions to overflow a single page
+	for i := 0; i < c.MaxPageSize+1; i++ {
+		// boundary.ConnectCli(t, ctx, newTargetId)
+		tClient.AuthorizeSession(ctx, newTargetId)
+	}
+
+	// List sessions
+	initialSessions, err := sClient.List(ctx, newProjectId)
+	require.NoError(t, err)
+
+	require.Len(t, initialSessions.Items, c.MaxPageSize+1)
+	assert.Equal(t, "complete", initialSessions.ResponseType)
+	assert.Empty(t, initialSessions.RemovedIds)
+	assert.NotEmpty(t, initialSessions.ListToken)
+	mapItems, ok := initialSessions.GetResponse().Map["items"]
+	require.True(t, ok)
+	mapSliceItems, ok := mapItems.([]any)
+	require.True(t, ok)
+	assert.Len(t, mapSliceItems, c.MaxPageSize+1)
+
+	// Create a new session
+	boundary.ConnectCli(t, ctx, newTargetId)
+
+	// List again, should have the new session
+	newSessions, err := sClient.List(ctx, newProjectId, sessions.WithListToken(initialSessions.ListToken))
+	require.NoError(t, err)
+
+	// Note that this will likely contain all the sessions,
+	// since they were created very shortly before the listing,
+	// and we add a 30 second buffer to the lower bound of update
+	// times when listing.
+	require.GreaterOrEqual(t, len(newSessions.Items), 1)
+	assert.Equal(t, "complete", newSessions.ResponseType)
+	assert.NotEmpty(t, newSessions.ListToken)
+	// Check that the response map contains all entries
+	mapItems, ok = newSessions.GetResponse().Map["items"]
+	require.True(t, ok)
+	mapSliceItems, ok = mapItems.([]any)
+	require.True(t, ok)
+	assert.GreaterOrEqual(t, len(mapSliceItems), 1)
+}