diff --git a/issue.go b/issue.go
index 0aa03b70..3d7a76cb 100644
--- a/issue.go
+++ b/issue.go
@@ -11,7 +11,6 @@ import (
 	"net/http"
 	"net/url"
 	"reflect"
-	"strconv"
 	"strings"
 	"time"
 
@@ -517,14 +516,23 @@ type CommentVisibility struct {
 // Default Pagination options
 type SearchOptions struct {
 	// StartAt: The starting index of the returned projects. Base index: 0.
-	StartAt int `url:"startAt,omitempty"`
+	StartAt int `url:"startAt,omitempty" json:"startAt,omitempty"`
 	// MaxResults: The maximum number of projects to return per page. Default: 50.
-	MaxResults int `url:"maxResults,omitempty"`
+	MaxResults int `url:"maxResults,omitempty" json:"maxResults,omitempty"`
 	// Expand: Expand specific sections in the returned issues
-	Expand string `url:"expand,omitempty"`
-	Fields []string
+	Expand string   `url:"expand,omitempty" json:"-"`
+	Fields []string `url:"fields,comma,omitempty" json:"fields,omitempty"`
 	// ValidateQuery: The validateQuery param offers control over whether to validate and how strictly to treat the validation. Default: strict.
-	ValidateQuery string `url:"validateQuery,omitempty"`
+	ValidateQuery string `url:"validateQuery,omitempty" json:"validateQuery,omitempty"`
+}
+
+// searchRequest is for the Search (with JQL) method to encode its inputs into a request whether it's POST or GET.
+type searchRequest struct {
+	// JQL is the query that the user passed.
+	JQL string `url:"jql,omitempty" json:"jql,omitempty"`
+	// ExpandArray is the array form of SearchOptions.Expand used for the POST/JSON version of the search request.
+	ExpandArray    []string `url:"-" json:"expand,omitempty"`
+	*SearchOptions `url:",omitempty" json:",omitempty"`
 }
 
 // searchResult is only a small wrapper around the Search (with JQL) method
@@ -1091,32 +1099,29 @@ func (s *IssueService) SearchWithContext(ctx context.Context, jql string, option
 	u := url.URL{
 		Path: "rest/api/2/search",
 	}
-	uv := url.Values{}
-	if jql != "" {
-		uv.Add("jql", jql)
+	r := searchRequest{
+		JQL:           jql,
+		SearchOptions: options,
 	}
-
-	if options != nil {
-		if options.StartAt != 0 {
-			uv.Add("startAt", strconv.Itoa(options.StartAt))
-		}
-		if options.MaxResults != 0 {
-			uv.Add("maxResults", strconv.Itoa(options.MaxResults))
-		}
-		if options.Expand != "" {
-			uv.Add("expand", options.Expand)
-		}
-		if strings.Join(options.Fields, ",") != "" {
-			uv.Add("fields", strings.Join(options.Fields, ","))
-		}
-		if options.ValidateQuery != "" {
-			uv.Add("validateQuery", options.ValidateQuery)
-		}
+	if options != nil && options.Expand != "" {
+		r.ExpandArray = strings.Split(options.Expand, ",")
 	}
 
+	uv, err := query.Values(r)
+	if err != nil {
+		return []Issue{}, nil, err
+	}
 	u.RawQuery = uv.Encode()
 
-	req, err := s.client.NewRequestWithContext(ctx, "GET", u.String(), nil)
+	var req *http.Request
+	if len(u.String()) > 2000 {
+		// If the JQL is too long, switch to the post method instead.
+		u.RawQuery = ""
+		req, err = s.client.NewRequestWithContext(ctx, "POST", u.String(), r)
+	} else {
+		req, err = s.client.NewRequestWithContext(ctx, "GET", u.String(), nil)
+	}
+
 	if err != nil {
 		return []Issue{}, nil, err
 	}
diff --git a/issue_test.go b/issue_test.go
index ceeff9a8..dc6d82b8 100644
--- a/issue_test.go
+++ b/issue_test.go
@@ -647,6 +647,45 @@ func TestIssueService_Search(t *testing.T) {
 	}
 }
 
+func TestIssueService_Search_Long_Query(t *testing.T) {
+	setup()
+	defer teardown()
+	testMux.HandleFunc("/rest/api/2/search", func(w http.ResponseWriter, r *http.Request) {
+		testMethod(t, r, "POST")
+		testRequestURL(t, r, "/rest/api/2/search")
+		w.WriteHeader(http.StatusOK)
+		fmt.Fprint(w, `{"expand": "schema,names","startAt": 1,"maxResults": 40,"total": 0,"issues": []}`)
+	})
+
+	opt := &SearchOptions{StartAt: 1, MaxResults: 40, Expand: "foo"}
+
+	// LONGKEY- is 8 characters; 250 x 8 is 2000, which is the limit for URL length.
+	keys := make([]string, 250)
+	for n := range keys {
+		keys[n] = fmt.Sprintf("LONGKEY-%d", n+1)
+	}
+
+	query := fmt.Sprintf("type = Bug and Key IN (%s)", strings.Join(keys, ","))
+	_, resp, err := testClient.Issue.Search(query, opt)
+
+	if resp == nil {
+		t.Errorf("Response given: %+v", resp)
+	}
+	if err != nil {
+		t.Errorf("Error given: %s", err)
+	}
+
+	if resp.StartAt != 1 {
+		t.Errorf("StartAt should populate with 1, %v given", resp.StartAt)
+	}
+	if resp.MaxResults != 40 {
+		t.Errorf("MaxResults should populate with 40, %v given", resp.MaxResults)
+	}
+	if resp.Total != 0 {
+		t.Errorf("Total should populate with 0, %v given", resp.Total)
+	}
+}
+
 func TestIssueService_SearchEmptyJQL(t *testing.T) {
 	setup()
 	defer teardown()