diff --git a/pkg/cmd/issue/list/http.go b/pkg/cmd/issue/list/http.go
index fcbfe7240..eb2c54330 100644
--- a/pkg/cmd/issue/list/http.go
+++ b/pkg/cmd/issue/list/http.go
@@ -4,6 +4,7 @@ import (
 	"fmt"
 
 	"github.com/cli/cli/v2/api"
+	fd "github.com/cli/cli/v2/internal/featuredetection"
 	"github.com/cli/cli/v2/internal/ghrepo"
 	prShared "github.com/cli/cli/v2/pkg/cmd/pr/shared"
 )
@@ -112,7 +113,12 @@ loop:
 	return &res, nil
 }
 
-func searchIssues(client *api.Client, repo ghrepo.Interface, filters prShared.FilterOptions, limit int) (*api.IssuesAndTotalCount, error) {
+func searchIssues(client *api.Client, detector fd.Detector, repo ghrepo.Interface, filters prShared.FilterOptions, limit int) (*api.IssuesAndTotalCount, error) {
+	features, err := detector.SearchFeatures()
+	if err != nil {
+		return nil, err
+	}
+
 	fragments := fmt.Sprintf("fragment issue on Issue {%s}", api.IssueGraphQL(filters.Fields))
 	query := fragments +
 		`query IssueSearch($repo: String!, $owner: String!, $type: SearchType!, $limit: Int, $after: String, $query: String!) {
@@ -143,18 +149,27 @@ func searchIssues(client *api.Client, repo ghrepo.Interface, filters prShared.Fi
 		}
 	}
 
-	filters.Repo = ghrepo.FullName(repo)
-	filters.Entity = "issue"
-	q := prShared.SearchQueryBuild(filters)
-
 	perPage := min(limit, 100)
 
 	variables := map[string]interface{}{
 		"owner": repo.RepoOwner(),
 		"repo":  repo.RepoName(),
-		"type":  "ISSUE",
 		"limit": perPage,
-		"query": q,
+	}
+
+	filters.Repo = ghrepo.FullName(repo)
+	filters.Entity = "issue"
+
+	if features.AdvancedIssueSearchAPI {
+		variables["query"] = prShared.SearchQueryBuild(filters, true)
+		if features.AdvancedIssueSearchAPIOptIn {
+			variables["type"] = "ISSUE_ADVANCED"
+		} else {
+			variables["type"] = "ISSUE"
+		}
+	} else {
+		variables["query"] = prShared.SearchQueryBuild(filters, false)
+		variables["type"] = "ISSUE"
 	}
 
 	ic := api.IssuesAndTotalCount{SearchCapped: limit > 1000}
diff --git a/pkg/cmd/issue/list/list.go b/pkg/cmd/issue/list/list.go
index 46c0e2cb0..241fbee02 100644
--- a/pkg/cmd/issue/list/list.go
+++ b/pkg/cmd/issue/list/list.go
@@ -165,8 +165,15 @@ func listRun(opts *ListOptions) error {
 	isTerminal := opts.IO.IsStdoutTTY()
 
 	if opts.WebMode {
+		searchFeatures, err := opts.Detector.SearchFeatures()
+		if err != nil {
+			return err
+		}
+
+		advancedSyntaxSupported := searchFeatures.AdvancedIssueSearchAPI && searchFeatures.AdvancedIssueSearchWebInIssuesTab
+
 		issueListURL := ghrepo.GenerateRepoURL(baseRepo, "issues")
-		openURL, err := prShared.ListURLWithQuery(issueListURL, filterOptions)
+		openURL, err := prShared.ListURLWithQuery(issueListURL, filterOptions, advancedSyntaxSupported)
 		if err != nil {
 			return err
 		}
@@ -181,7 +188,7 @@ func listRun(opts *ListOptions) error {
 		filterOptions.Fields = opts.Exporter.Fields()
 	}
 
-	listResult, err := issueList(httpClient, baseRepo, filterOptions, opts.LimitResults)
+	listResult, err := issueList(httpClient, opts.Detector, baseRepo, filterOptions, opts.LimitResults)
 	if err != nil {
 		return err
 	}
@@ -212,7 +219,7 @@ func listRun(opts *ListOptions) error {
 	return nil
 }
 
-func issueList(client *http.Client, repo ghrepo.Interface, filters prShared.FilterOptions, limit int) (*api.IssuesAndTotalCount, error) {
+func issueList(client *http.Client, detector fd.Detector, repo ghrepo.Interface, filters prShared.FilterOptions, limit int) (*api.IssuesAndTotalCount, error) {
 	apiClient := api.NewClientFromHTTP(client)
 
 	if filters.Search != "" || len(filters.Labels) > 0 || filters.Milestone != "" {
@@ -224,7 +231,7 @@ func issueList(client *http.Client, repo ghrepo.Interface, filters prShared.Filt
 			filters.Milestone = milestone.Title
 		}
 
-		return searchIssues(apiClient, repo, filters, limit)
+		return searchIssues(apiClient, detector, repo, filters, limit)
 	}
 
 	var err error
diff --git a/pkg/cmd/issue/list/list_test.go b/pkg/cmd/issue/list/list_test.go
index 852f0a46b..b88414d43 100644
--- a/pkg/cmd/issue/list/list_test.go
+++ b/pkg/cmd/issue/list/list_test.go
@@ -11,6 +11,7 @@ import (
 	"github.com/cli/cli/v2/api"
 	"github.com/cli/cli/v2/internal/browser"
 	"github.com/cli/cli/v2/internal/config"
+	fd "github.com/cli/cli/v2/internal/featuredetection"
 	"github.com/cli/cli/v2/internal/gh"
 	"github.com/cli/cli/v2/internal/ghrepo"
 	"github.com/cli/cli/v2/internal/run"
@@ -210,6 +211,7 @@ func TestIssueList_web(t *testing.T) {
 		BaseRepo: func() (ghrepo.Interface, error) {
 			return ghrepo.New("OWNER", "REPO"), nil
 		},
+		Detector:     fd.AdvancedIssueSearchUnsupported(),
 		WebMode:      true,
 		State:        "all",
 		Assignee:     "peter",
@@ -230,9 +232,10 @@ func TestIssueList_web(t *testing.T) {
 
 func Test_issueList(t *testing.T) {
 	type args struct {
-		repo    ghrepo.Interface
-		filters prShared.FilterOptions
-		limit   int
+		detector fd.Detector
+		repo     ghrepo.Interface
+		filters  prShared.FilterOptions
+		limit    int
 	}
 	tests := []struct {
 		name      string
@@ -243,8 +246,9 @@ func Test_issueList(t *testing.T) {
 		{
 			name: "default",
 			args: args{
-				limit: 30,
-				repo:  ghrepo.New("OWNER", "REPO"),
+				detector: fd.AdvancedIssueSearchUnsupported(),
+				limit:    30,
+				repo:     ghrepo.New("OWNER", "REPO"),
 				filters: prShared.FilterOptions{
 					Entity: "issue",
 					State:  "open",
@@ -270,8 +274,9 @@ func Test_issueList(t *testing.T) {
 		{
 			name: "milestone by number",
 			args: args{
-				limit: 30,
-				repo:  ghrepo.New("OWNER", "REPO"),
+				detector: fd.AdvancedIssueSearchUnsupported(),
+				limit:    30,
+				repo:     ghrepo.New("OWNER", "REPO"),
 				filters: prShared.FilterOptions{
 					Entity:    "issue",
 					State:     "open",
@@ -309,8 +314,9 @@ func Test_issueList(t *testing.T) {
 		{
 			name: "milestone by title",
 			args: args{
-				limit: 30,
-				repo:  ghrepo.New("OWNER", "REPO"),
+				detector: fd.AdvancedIssueSearchUnsupported(),
+				limit:    30,
+				repo:     ghrepo.New("OWNER", "REPO"),
 				filters: prShared.FilterOptions{
 					Entity:    "issue",
 					State:     "open",
@@ -341,8 +347,9 @@ func Test_issueList(t *testing.T) {
 		{
 			name: "@me syntax",
 			args: args{
-				limit: 30,
-				repo:  ghrepo.New("OWNER", "REPO"),
+				detector: fd.AdvancedIssueSearchUnsupported(),
+				limit:    30,
+				repo:     ghrepo.New("OWNER", "REPO"),
 				filters: prShared.FilterOptions{
 					Entity:   "issue",
 					State:    "open",
@@ -377,8 +384,9 @@ func Test_issueList(t *testing.T) {
 		{
 			name: "@me with search",
 			args: args{
-				limit: 30,
-				repo:  ghrepo.New("OWNER", "REPO"),
+				detector: fd.AdvancedIssueSearchUnsupported(),
+				limit:    30,
+				repo:     ghrepo.New("OWNER", "REPO"),
 				filters: prShared.FilterOptions{
 					Entity:   "issue",
 					State:    "open",
@@ -412,8 +420,9 @@ func Test_issueList(t *testing.T) {
 		{
 			name: "with labels",
 			args: args{
-				limit: 30,
-				repo:  ghrepo.New("OWNER", "REPO"),
+				detector: fd.AdvancedIssueSearchUnsupported(),
+				limit:    30,
+				repo:     ghrepo.New("OWNER", "REPO"),
 				filters: prShared.FilterOptions{
 					Entity: "issue",
 					State:  "open",
@@ -450,7 +459,7 @@ func Test_issueList(t *testing.T) {
 				tt.httpStubs(httpreg)
 			}
 			client := &http.Client{Transport: httpreg}
-			_, err := issueList(client, tt.args.repo, tt.args.filters, tt.args.limit)
+			_, err := issueList(client, tt.args.detector, tt.args.repo, tt.args.filters, tt.args.limit)
 			if tt.wantErr {
 				assert.Error(t, err)
 			} else {
@@ -507,6 +516,7 @@ func TestIssueList_withProjectItems(t *testing.T) {
 	client := &http.Client{Transport: reg}
 	issuesAndTotalCount, err := issueList(
 		client,
+		fd.AdvancedIssueSearchUnsupported(),
 		ghrepo.New("OWNER", "REPO"),
 		prShared.FilterOptions{
 			Entity: "issue",
@@ -581,6 +591,7 @@ func TestIssueList_Search_withProjectItems(t *testing.T) {
 	client := &http.Client{Transport: reg}
 	issuesAndTotalCount, err := issueList(
 		client,
+		fd.AdvancedIssueSearchUnsupported(),
 		ghrepo.New("OWNER", "REPO"),
 		prShared.FilterOptions{
 			Entity: "issue",
diff --git a/pkg/cmd/pr/list/http.go b/pkg/cmd/pr/list/http.go
index 4c69af708..24a303e43 100644
--- a/pkg/cmd/pr/list/http.go
+++ b/pkg/cmd/pr/list/http.go
@@ -5,6 +5,7 @@ import (
 	"net/http"
 
 	"github.com/cli/cli/v2/api"
+	fd "github.com/cli/cli/v2/internal/featuredetection"
 	"github.com/cli/cli/v2/internal/ghrepo"
 	prShared "github.com/cli/cli/v2/pkg/cmd/pr/shared"
 )
@@ -13,9 +14,9 @@ func shouldUseSearch(filters prShared.FilterOptions) bool {
 	return filters.Draft != nil || filters.Author != "" || filters.Assignee != "" || filters.Search != "" || len(filters.Labels) > 0
 }
 
-func listPullRequests(httpClient *http.Client, repo ghrepo.Interface, filters prShared.FilterOptions, limit int) (*api.PullRequestAndTotalCount, error) {
+func listPullRequests(httpClient *http.Client, detector fd.Detector, repo ghrepo.Interface, filters prShared.FilterOptions, limit int) (*api.PullRequestAndTotalCount, error) {
 	if shouldUseSearch(filters) {
-		return searchPullRequests(httpClient, repo, filters, limit)
+		return searchPullRequests(httpClient, detector, repo, filters, limit)
 	}
 
 	return prShared.NewLister(httpClient).List(prShared.ListOptions{
@@ -28,7 +29,12 @@ func listPullRequests(httpClient *http.Client, repo ghrepo.Interface, filters pr
 	})
 }
 
-func searchPullRequests(httpClient *http.Client, repo ghrepo.Interface, filters prShared.FilterOptions, limit int) (*api.PullRequestAndTotalCount, error) {
+func searchPullRequests(httpClient *http.Client, detector fd.Detector, repo ghrepo.Interface, filters prShared.FilterOptions, limit int) (*api.PullRequestAndTotalCount, error) {
+	features, err := detector.SearchFeatures()
+	if err != nil {
+		return nil, err
+	}
+
 	type response struct {
 		Search struct {
 			Nodes    []api.PullRequest
@@ -44,10 +50,11 @@ func searchPullRequests(httpClient *http.Client, repo ghrepo.Interface, filters
 	query := fragment + `
 		query PullRequestSearch(
 			$q: String!,
+			$type: SearchType!,
 			$limit: Int!,
 			$endCursor: String,
 		) {
-			search(query: $q, type: ISSUE, first: $limit, after: $endCursor) {
+			search(query: $q, type: $type, first: $limit, after: $endCursor) {
 				issueCount
 				nodes {
 					...pr
@@ -59,12 +66,24 @@ func searchPullRequests(httpClient *http.Client, repo ghrepo.Interface, filters
 			}
 		}`
 
+	variables := map[string]interface{}{}
+
 	filters.Repo = ghrepo.FullName(repo)
 	filters.Entity = "pr"
-	q := prShared.SearchQueryBuild(filters)
+
+	if features.AdvancedIssueSearchAPI {
+		variables["q"] = prShared.SearchQueryBuild(filters, true)
+		if features.AdvancedIssueSearchAPIOptIn {
+			variables["type"] = "ISSUE_ADVANCED"
+		} else {
+			variables["type"] = "ISSUE"
+		}
+	} else {
+		variables["q"] = prShared.SearchQueryBuild(filters, false)
+		variables["type"] = "ISSUE"
+	}
 
 	pageLimit := min(limit, 100)
-	variables := map[string]interface{}{"q": q}
 
 	res := api.PullRequestAndTotalCount{SearchCapped: limit > 1000}
 	var check = make(map[int]struct{})
diff --git a/pkg/cmd/pr/list/http_test.go b/pkg/cmd/pr/list/http_test.go
index 1aa16ae1d..4f796906a 100644
--- a/pkg/cmd/pr/list/http_test.go
+++ b/pkg/cmd/pr/list/http_test.go
@@ -5,6 +5,7 @@ import (
 	"reflect"
 	"testing"
 
+	fd "github.com/cli/cli/v2/internal/featuredetection"
 	"github.com/cli/cli/v2/internal/ghrepo"
 	prShared "github.com/cli/cli/v2/pkg/cmd/pr/shared"
 	"github.com/cli/cli/v2/pkg/httpmock"
@@ -12,9 +13,10 @@ import (
 
 func Test_ListPullRequests(t *testing.T) {
 	type args struct {
-		repo    ghrepo.Interface
-		filters prShared.FilterOptions
-		limit   int
+		detector fd.Detector
+		repo     ghrepo.Interface
+		filters  prShared.FilterOptions
+		limit    int
 	}
 	tests := []struct {
 		name     string
@@ -25,8 +27,9 @@ func Test_ListPullRequests(t *testing.T) {
 		{
 			name: "default",
 			args: args{
-				repo:  ghrepo.New("OWNER", "REPO"),
-				limit: 30,
+				detector: fd.AdvancedIssueSearchUnsupported(),
+				repo:     ghrepo.New("OWNER", "REPO"),
+				limit:    30,
 				filters: prShared.FilterOptions{
 					State: "open",
 				},
@@ -50,8 +53,9 @@ func Test_ListPullRequests(t *testing.T) {
 		{
 			name: "closed",
 			args: args{
-				repo:  ghrepo.New("OWNER", "REPO"),
-				limit: 30,
+				detector: fd.AdvancedIssueSearchUnsupported(),
+				repo:     ghrepo.New("OWNER", "REPO"),
+				limit:    30,
 				filters: prShared.FilterOptions{
 					State: "closed",
 				},
@@ -75,8 +79,9 @@ func Test_ListPullRequests(t *testing.T) {
 		{
 			name: "with labels",
 			args: args{
-				repo:  ghrepo.New("OWNER", "REPO"),
-				limit: 30,
+				detector: fd.AdvancedIssueSearchUnsupported(),
+				repo:     ghrepo.New("OWNER", "REPO"),
+				limit:    30,
 				filters: prShared.FilterOptions{
 					State:  "open",
 					Labels: []string{"hello", "one world"},
@@ -88,6 +93,7 @@ func Test_ListPullRequests(t *testing.T) {
 					httpmock.GraphQLQuery(`{"data":{}}`, func(query string, vars map[string]interface{}) {
 						want := map[string]interface{}{
 							"q":     `label:"one world" label:hello repo:OWNER/REPO state:open type:pr`,
+							"type":  "ISSUE",
 							"limit": float64(30),
 						}
 						if !reflect.DeepEqual(vars, want) {
@@ -99,8 +105,9 @@ func Test_ListPullRequests(t *testing.T) {
 		{
 			name: "with author",
 			args: args{
-				repo:  ghrepo.New("OWNER", "REPO"),
-				limit: 30,
+				detector: fd.AdvancedIssueSearchUnsupported(),
+				repo:     ghrepo.New("OWNER", "REPO"),
+				limit:    30,
 				filters: prShared.FilterOptions{
 					State:  "open",
 					Author: "monalisa",
@@ -112,6 +119,7 @@ func Test_ListPullRequests(t *testing.T) {
 					httpmock.GraphQLQuery(`{"data":{}}`, func(query string, vars map[string]interface{}) {
 						want := map[string]interface{}{
 							"q":     "author:monalisa repo:OWNER/REPO state:open type:pr",
+							"type":  "ISSUE",
 							"limit": float64(30),
 						}
 						if !reflect.DeepEqual(vars, want) {
@@ -123,8 +131,9 @@ func Test_ListPullRequests(t *testing.T) {
 		{
 			name: "with search",
 			args: args{
-				repo:  ghrepo.New("OWNER", "REPO"),
-				limit: 30,
+				detector: fd.AdvancedIssueSearchUnsupported(),
+				repo:     ghrepo.New("OWNER", "REPO"),
+				limit:    30,
 				filters: prShared.FilterOptions{
 					State:  "open",
 					Search: "one world in:title",
@@ -136,6 +145,7 @@ func Test_ListPullRequests(t *testing.T) {
 					httpmock.GraphQLQuery(`{"data":{}}`, func(query string, vars map[string]interface{}) {
 						want := map[string]interface{}{
 							"q":     "one world in:title repo:OWNER/REPO state:open type:pr",
+							"type":  "ISSUE",
 							"limit": float64(30),
 						}
 						if !reflect.DeepEqual(vars, want) {
@@ -153,7 +163,7 @@ func Test_ListPullRequests(t *testing.T) {
 			}
 			httpClient := &http.Client{Transport: reg}
 
-			_, err := listPullRequests(httpClient, tt.args.repo, tt.args.filters, tt.args.limit)
+			_, err := listPullRequests(httpClient, tt.args.detector, tt.args.repo, tt.args.filters, tt.args.limit)
 			if (err != nil) != tt.wantErr {
 				t.Errorf("ListPullRequests() error = %v, wantErr %v", err, tt.wantErr)
 				return
diff --git a/pkg/cmd/pr/list/list.go b/pkg/cmd/pr/list/list.go
index 7188df1a5..383e2b5fb 100644
--- a/pkg/cmd/pr/list/list.go
+++ b/pkg/cmd/pr/list/list.go
@@ -10,6 +10,7 @@ import (
 	"github.com/MakeNowJust/heredoc"
 	"github.com/cli/cli/v2/api"
 	"github.com/cli/cli/v2/internal/browser"
+	fd "github.com/cli/cli/v2/internal/featuredetection"
 	"github.com/cli/cli/v2/internal/ghrepo"
 	"github.com/cli/cli/v2/internal/tableprinter"
 	"github.com/cli/cli/v2/internal/text"
@@ -24,6 +25,7 @@ type ListOptions struct {
 	IO         *iostreams.IOStreams
 	BaseRepo   func() (ghrepo.Interface, error)
 	Browser    browser.Browser
+	Detector   fd.Detector
 
 	WebMode      bool
 	LimitResults int
@@ -142,6 +144,11 @@ func listRun(opts *ListOptions) error {
 		return err
 	}
 
+	if opts.Detector == nil {
+		cachedClient := api.NewCachedHTTPClient(httpClient, time.Hour*24)
+		opts.Detector = fd.NewDetector(cachedClient, baseRepo.RepoHost())
+	}
+
 	prState := strings.ToLower(opts.State)
 	if prState == "open" && shared.QueryHasStateClause(opts.Search) {
 		prState = ""
@@ -164,7 +171,11 @@ func listRun(opts *ListOptions) error {
 	}
 	if opts.WebMode {
 		prListURL := ghrepo.GenerateRepoURL(baseRepo, "pulls")
-		openURL, err := shared.ListURLWithQuery(prListURL, filters)
+
+		// TODO(babakks): As of August 2025, the advanced issue search syntax is
+		// not supported in Pull Requests tab of repositories. When it's supported
+		// we can change the argument to true.
+		openURL, err := shared.ListURLWithQuery(prListURL, filters, false)
 		if err != nil {
 			return err
 		}
@@ -175,7 +186,7 @@ func listRun(opts *ListOptions) error {
 		return opts.Browser.Browse(openURL)
 	}
 
-	listResult, err := listPullRequests(httpClient, baseRepo, filters, opts.LimitResults)
+	listResult, err := listPullRequests(httpClient, opts.Detector, baseRepo, filters, opts.LimitResults)
 	if err != nil {
 		return err
 	}
diff --git a/pkg/cmd/pr/list/list_test.go b/pkg/cmd/pr/list/list_test.go
index ecd0326b5..6a7c2815a 100644
--- a/pkg/cmd/pr/list/list_test.go
+++ b/pkg/cmd/pr/list/list_test.go
@@ -11,6 +11,7 @@ import (
 	"github.com/MakeNowJust/heredoc"
 	"github.com/cli/cli/v2/api"
 	"github.com/cli/cli/v2/internal/browser"
+	fd "github.com/cli/cli/v2/internal/featuredetection"
 	"github.com/cli/cli/v2/internal/ghrepo"
 	"github.com/cli/cli/v2/internal/run"
 	prShared "github.com/cli/cli/v2/pkg/cmd/pr/shared"
@@ -23,7 +24,7 @@ import (
 	"github.com/stretchr/testify/require"
 )
 
-func runCommand(rt http.RoundTripper, isTTY bool, cli string) (*test.CmdOut, error) {
+func runCommand(rt http.RoundTripper, detector fd.Detector, isTTY bool, cli string) (*test.CmdOut, error) {
 	ios, _, stdout, stderr := iostreams.Test()
 	ios.SetStdoutTTY(isTTY)
 	ios.SetStdinTTY(isTTY)
@@ -47,6 +48,7 @@ func runCommand(rt http.RoundTripper, isTTY bool, cli string) (*test.CmdOut, err
 
 	cmd := NewCmdList(factory, func(opts *ListOptions) error {
 		opts.Now = fakeNow
+		opts.Detector = detector
 		return listRun(opts)
 	})
 
@@ -78,7 +80,7 @@ func TestPRList(t *testing.T) {
 
 	http.Register(httpmock.GraphQL(`query PullRequestList\b`), httpmock.FileResponse("./fixtures/prList.json"))
 
-	output, err := runCommand(http, true, "")
+	output, err := runCommand(http, fd.AdvancedIssueSearchUnsupported(), true, "")
 	if err != nil {
 		t.Fatal(err)
 	}
@@ -101,7 +103,7 @@ func TestPRList_nontty(t *testing.T) {
 
 	http.Register(httpmock.GraphQL(`query PullRequestList\b`), httpmock.FileResponse("./fixtures/prList.json"))
 
-	output, err := runCommand(http, false, "")
+	output, err := runCommand(http, fd.AdvancedIssueSearchUnsupported(), false, "")
 	if err != nil {
 		t.Fatal(err)
 	}
@@ -124,7 +126,7 @@ func TestPRList_filtering(t *testing.T) {
 			assert.Equal(t, []interface{}{"OPEN", "CLOSED", "MERGED"}, params["state"].([]interface{}))
 		}))
 
-	output, err := runCommand(http, true, `-s all`)
+	output, err := runCommand(http, fd.AdvancedIssueSearchUnsupported(), true, `-s all`)
 	assert.Error(t, err)
 
 	assert.Equal(t, "", output.String())
@@ -139,7 +141,7 @@ func TestPRList_filteringRemoveDuplicate(t *testing.T) {
 		httpmock.GraphQL(`query PullRequestList\b`),
 		httpmock.FileResponse("./fixtures/prListWithDuplicates.json"))
 
-	output, err := runCommand(http, true, "")
+	output, err := runCommand(http, fd.AdvancedIssueSearchUnsupported(), true, "")
 	if err != nil {
 		t.Fatal(err)
 	}
@@ -162,7 +164,7 @@ func TestPRList_filteringClosed(t *testing.T) {
 			assert.Equal(t, []interface{}{"CLOSED", "MERGED"}, params["state"].([]interface{}))
 		}))
 
-	_, err := runCommand(http, true, `-s closed`)
+	_, err := runCommand(http, fd.AdvancedIssueSearchUnsupported(), true, `-s closed`)
 	assert.Error(t, err)
 }
 
@@ -176,7 +178,7 @@ func TestPRList_filteringHeadBranch(t *testing.T) {
 			assert.Equal(t, interface{}("bug-fix"), params["headBranch"])
 		}))
 
-	_, err := runCommand(http, true, `-H bug-fix`)
+	_, err := runCommand(http, fd.AdvancedIssueSearchUnsupported(), true, `-H bug-fix`)
 	assert.Error(t, err)
 }
 
@@ -190,7 +192,7 @@ func TestPRList_filteringAssignee(t *testing.T) {
 			assert.Equal(t, `assignee:hubot base:develop is:merged label:"needs tests" repo:OWNER/REPO type:pr`, params["q"].(string))
 		}))
 
-	_, err := runCommand(http, true, `-s merged -l "needs tests" -a hubot -B develop`)
+	_, err := runCommand(http, fd.AdvancedIssueSearchUnsupported(), true, `-s merged -l "needs tests" -a hubot -B develop`)
 	assert.Error(t, err)
 }
 
@@ -223,7 +225,7 @@ func TestPRList_filteringDraft(t *testing.T) {
 					assert.Equal(t, test.expectedQuery, params["q"].(string))
 				}))
 
-			_, err := runCommand(http, true, test.cli)
+			_, err := runCommand(http, fd.AdvancedIssueSearchUnsupported(), true, test.cli)
 			assert.Error(t, err)
 		})
 	}
@@ -268,7 +270,7 @@ func TestPRList_filteringAuthor(t *testing.T) {
 					assert.Equal(t, test.expectedQuery, params["q"].(string))
 				}))
 
-			_, err := runCommand(http, true, test.cli)
+			_, err := runCommand(http, fd.AdvancedIssueSearchUnsupported(), true, test.cli)
 			assert.Error(t, err)
 		})
 	}
@@ -277,7 +279,7 @@ func TestPRList_filteringAuthor(t *testing.T) {
 func TestPRList_withInvalidLimitFlag(t *testing.T) {
 	http := initFakeHTTP()
 	defer http.Verify(t)
-	_, err := runCommand(http, true, `--limit=0`)
+	_, err := runCommand(http, fd.AdvancedIssueSearchUnsupported(), true, `--limit=0`)
 	assert.EqualError(t, err, "invalid value for --limit: 0")
 }
 
@@ -312,7 +314,7 @@ func TestPRList_web(t *testing.T) {
 			_, cmdTeardown := run.Stub()
 			defer cmdTeardown(t)
 
-			output, err := runCommand(http, true, "--web "+test.cli)
+			output, err := runCommand(http, fd.AdvancedIssueSearchUnsupported(), true, "--web "+test.cli)
 			if err != nil {
 				t.Errorf("error running command `pr list` with `--web` flag: %v", err)
 			}
@@ -370,6 +372,7 @@ func TestPRList_withProjectItems(t *testing.T) {
 	client := &http.Client{Transport: reg}
 	prsAndTotalCount, err := listPullRequests(
 		client,
+		fd.AdvancedIssueSearchUnsupported(),
 		ghrepo.New("OWNER", "REPO"),
 		prShared.FilterOptions{
 			Entity: "pr",
@@ -433,12 +436,14 @@ func TestPRList_Search_withProjectItems(t *testing.T) {
 			require.Equal(t, map[string]interface{}{
 				"limit": float64(30),
 				"q":     "just used to force the search API branch repo:OWNER/REPO state:open type:pr",
+				"type":  "ISSUE",
 			}, params)
 		}))
 
 	client := &http.Client{Transport: reg}
 	prsAndTotalCount, err := listPullRequests(
 		client,
+		fd.AdvancedIssueSearchUnsupported(),
 		ghrepo.New("OWNER", "REPO"),
 		prShared.FilterOptions{
 			Entity: "pr",
diff --git a/pkg/cmd/pr/shared/params.go b/pkg/cmd/pr/shared/params.go
index c3315aeae..742b3795b 100644
--- a/pkg/cmd/pr/shared/params.go
+++ b/pkg/cmd/pr/shared/params.go
@@ -186,20 +186,20 @@ func (opts *FilterOptions) IsDefault() bool {
 	return true
 }
 
-func ListURLWithQuery(listURL string, options FilterOptions) (string, error) {
+func ListURLWithQuery(listURL string, options FilterOptions, advancedIssueSearchSyntax bool) (string, error) {
 	u, err := url.Parse(listURL)
 	if err != nil {
 		return "", err
 	}
 
 	params := u.Query()
-	params.Set("q", SearchQueryBuild(options))
+	params.Set("q", SearchQueryBuild(options, advancedIssueSearchSyntax))
 	u.RawQuery = params.Encode()
 
 	return u.String(), nil
 }
 
-func SearchQueryBuild(options FilterOptions) string {
+func SearchQueryBuild(options FilterOptions, advancedIssueSearchSyntax bool) string {
 	var is, state string
 	switch options.State {
 	case "open", "closed":
@@ -207,7 +207,7 @@ func SearchQueryBuild(options FilterOptions) string {
 	case "merged":
 		is = "merged"
 	}
-	q := search.Query{
+	query := search.Query{
 		Qualifiers: search.Qualifiers{
 			Assignee:  options.Assignee,
 			Author:    options.Author,
@@ -223,10 +223,18 @@ func SearchQueryBuild(options FilterOptions) string {
 			Type:      options.Entity,
 		},
 	}
-	if options.Search != "" {
-		return fmt.Sprintf("%s %s", options.Search, q.String())
+
+	var q string
+	if advancedIssueSearchSyntax {
+		q = query.AdvancedIssueSearchString()
+	} else {
+		q = query.String()
 	}
-	return q.String()
+
+	if options.Search != "" {
+		return fmt.Sprintf("%s %s", options.Search, q)
+	}
+	return q
 }
 
 func QueryHasStateClause(searchQuery string) bool {
diff --git a/pkg/cmd/pr/shared/params_test.go b/pkg/cmd/pr/shared/params_test.go
index 3c95a9a5d..5cc73bc2f 100644
--- a/pkg/cmd/pr/shared/params_test.go
+++ b/pkg/cmd/pr/shared/params_test.go
@@ -19,8 +19,9 @@ func Test_listURLWithQuery(t *testing.T) {
 	falseBool := false
 
 	type args struct {
-		listURL string
-		options FilterOptions
+		listURL                   string
+		options                   FilterOptions
+		advancedIssueSearchSyntax bool
 	}
 
 	tests := []struct {
@@ -101,7 +102,7 @@ func Test_listURLWithQuery(t *testing.T) {
 	}
 	for _, tt := range tests {
 		t.Run(tt.name, func(t *testing.T) {
-			got, err := ListURLWithQuery(tt.args.listURL, tt.args.options)
+			got, err := ListURLWithQuery(tt.args.listURL, tt.args.options, tt.args.advancedIssueSearchSyntax)
 			if (err != nil) != tt.wantErr {
 				t.Errorf("listURLWithQuery() error = %v, wantErr %v", err, tt.wantErr)
 				return