diff --git a/custom/conf/app.example.ini b/custom/conf/app.example.ini
index c2b721b0cfbd..44445579bdee 100644
--- a/custom/conf/app.example.ini
+++ b/custom/conf/app.example.ini
@@ -1048,6 +1048,9 @@ LEVEL = Info
 ;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;
 ;; List of reasons why a Pull Request or Issue can be locked
 ;LOCK_REASONS = Too heated,Off-topic,Resolved,Spam
+;; Maximum number of pinned Issues
+;; Set to 0 to disable pinning Issues
+;MAX_PINNED = 3
 
 ;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;
 ;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;;
diff --git a/docs/content/doc/administration/config-cheat-sheet.en-us.md b/docs/content/doc/administration/config-cheat-sheet.en-us.md
index 9616be586d35..1fa4abcef299 100644
--- a/docs/content/doc/administration/config-cheat-sheet.en-us.md
+++ b/docs/content/doc/administration/config-cheat-sheet.en-us.md
@@ -141,6 +141,7 @@ In addition there is _`StaticRootPath`_ which can be set as a built-in at build
 ### Repository - Issue (`repository.issue`)
 
 - `LOCK_REASONS`: **Too heated,Off-topic,Resolved,Spam**: A list of reasons why a Pull Request or Issue can be locked
+- `MAX_PINNED`: **3**: Maximum number of pinned Issues. Set to 0 to disable pinning Issues.
 
 ### Repository - Upload (`repository.upload`)
 
diff --git a/models/issues/comment.go b/models/issues/comment.go
index bf2bbfa4145b..e5c90f265e1f 100644
--- a/models/issues/comment.go
+++ b/models/issues/comment.go
@@ -107,6 +107,8 @@ const (
 	CommentTypePRScheduledToAutoMerge   // 34 pr was scheduled to auto merge when checks succeed
 	CommentTypePRUnScheduledToAutoMerge // 35 pr was un scheduled to auto merge when checks succeed
 
+	CommentTypePin   // 36 pin Issue
+	CommentTypeUnpin // 37 unpin Issue
 )
 
 var commentStrings = []string{
@@ -146,6 +148,8 @@ var commentStrings = []string{
 	"change_issue_ref",
 	"pull_scheduled_merge",
 	"pull_cancel_scheduled_merge",
+	"pin",
+	"unpin",
 }
 
 func (t CommentType) String() string {
diff --git a/models/issues/issue.go b/models/issues/issue.go
index fc046d273c98..5015824e9b34 100644
--- a/models/issues/issue.go
+++ b/models/issues/issue.go
@@ -14,6 +14,7 @@ import (
 	repo_model "code.gitea.io/gitea/models/repo"
 	user_model "code.gitea.io/gitea/models/user"
 	"code.gitea.io/gitea/modules/log"
+	"code.gitea.io/gitea/modules/setting"
 	api "code.gitea.io/gitea/modules/structs"
 	"code.gitea.io/gitea/modules/timeutil"
 	"code.gitea.io/gitea/modules/util"
@@ -116,6 +117,7 @@ type Issue struct {
 	PullRequest      *PullRequest     `xorm:"-"`
 	NumComments      int
 	Ref              string
+	PinOrder         int `xorm:"DEFAULT 0"`
 
 	DeadlineUnix timeutil.TimeStamp `xorm:"INDEX"`
 
@@ -684,3 +686,180 @@ func (issue *Issue) GetExternalID() int64 { return issue.OriginalAuthorID }
 func (issue *Issue) HasOriginalAuthor() bool {
 	return issue.OriginalAuthor != "" && issue.OriginalAuthorID != 0
 }
+
+// IsPinned returns if a Issue is pinned
+func (issue *Issue) IsPinned() bool {
+	return issue.PinOrder != 0
+}
+
+// Pin pins a Issue
+func (issue *Issue) Pin(ctx context.Context, user *user_model.User) error {
+	// If the Issue is already pinned, we don't need to pin it twice
+	if issue.IsPinned() {
+		return nil
+	}
+
+	var maxPin int
+	_, err := db.GetEngine(ctx).SQL("SELECT MAX(pin_order) FROM issue WHERE repo_id = ? AND is_pull = ?", issue.RepoID, issue.IsPull).Get(&maxPin)
+	if err != nil {
+		return err
+	}
+
+	// Check if the maximum allowed Pins reached
+	if maxPin >= setting.Repository.Issue.MaxPinned {
+		return fmt.Errorf("You have reached the max number of pinned Issues")
+	}
+
+	_, err = db.GetEngine(ctx).Table("issue").
+		Where("id = ?", issue.ID).
+		Update(map[string]interface{}{
+			"pin_order": maxPin + 1,
+		})
+	if err != nil {
+		return err
+	}
+
+	// Add the pin event to the history
+	opts := &CreateCommentOptions{
+		Type:  CommentTypePin,
+		Doer:  user,
+		Repo:  issue.Repo,
+		Issue: issue,
+	}
+	if _, err = CreateComment(ctx, opts); err != nil {
+		return err
+	}
+
+	return nil
+}
+
+// UnpinIssue unpins a Issue
+func (issue *Issue) Unpin(ctx context.Context, user *user_model.User) error {
+	// If the Issue is not pinned, we don't need to unpin it
+	if !issue.IsPinned() {
+		return nil
+	}
+
+	// This sets the Pin for all Issues that come after the unpined Issue to the correct value
+	_, err := db.GetEngine(ctx).Exec("UPDATE issue SET pin_order = pin_order - 1 WHERE repo_id = ? AND is_pull = ? AND pin_order > ?", issue.RepoID, issue.IsPull, issue.PinOrder)
+	if err != nil {
+		return err
+	}
+
+	_, err = db.GetEngine(ctx).Table("issue").
+		Where("id = ?", issue.ID).
+		Update(map[string]interface{}{
+			"pin_order": 0,
+		})
+	if err != nil {
+		return err
+	}
+
+	// Add the unpin event to the history
+	opts := &CreateCommentOptions{
+		Type:  CommentTypeUnpin,
+		Doer:  user,
+		Repo:  issue.Repo,
+		Issue: issue,
+	}
+	if _, err = CreateComment(ctx, opts); err != nil {
+		return err
+	}
+
+	return nil
+}
+
+// PinOrUnpin pins or unpins a Issue
+func (issue *Issue) PinOrUnpin(ctx context.Context, user *user_model.User) error {
+	if !issue.IsPinned() {
+		return issue.Pin(ctx, user)
+	}
+
+	return issue.Unpin(ctx, user)
+}
+
+// MovePin moves a Pinned Issue to a new Position
+func (issue *Issue) MovePin(ctx context.Context, newPosition int) error {
+	// If the Issue is not pinned, we can't move them
+	if !issue.IsPinned() {
+		return nil
+	}
+
+	if newPosition < 1 {
+		return fmt.Errorf("The Position can't be lower than 1")
+	}
+
+	dbctx, committer, err := db.TxContext(ctx)
+	if err != nil {
+		return err
+	}
+	defer committer.Close()
+
+	var maxPin int
+	_, err = db.GetEngine(dbctx).SQL("SELECT MAX(pin_order) FROM issue WHERE repo_id = ? AND is_pull = ?", issue.RepoID, issue.IsPull).Get(&maxPin)
+	if err != nil {
+		return err
+	}
+
+	// If the new Position bigger than the current Maximum, set it to the Maximum
+	if newPosition > maxPin+1 {
+		newPosition = maxPin + 1
+	}
+
+	// Lower the Position of all Pinned Issue that came after the current Position
+	_, err = db.GetEngine(dbctx).Exec("UPDATE issue SET pin_order = pin_order - 1 WHERE repo_id = ? AND is_pull = ? AND pin_order > ?", issue.RepoID, issue.IsPull, issue.PinOrder)
+	if err != nil {
+		return err
+	}
+
+	// Higher the Position of all Pinned Issues that comes after the new Position
+	_, err = db.GetEngine(dbctx).Exec("UPDATE issue SET pin_order = pin_order + 1 WHERE repo_id = ? AND is_pull = ? AND pin_order >= ?", issue.RepoID, issue.IsPull, newPosition)
+	if err != nil {
+		return err
+	}
+
+	_, err = db.GetEngine(dbctx).Table("issue").
+		Where("id = ?", issue.ID).
+		Update(map[string]interface{}{
+			"pin_order": newPosition,
+		})
+	if err != nil {
+		return err
+	}
+
+	return committer.Commit()
+}
+
+// GetPinnedIssues returns the pinned Issues for the given Repo and type
+func GetPinnedIssues(ctx context.Context, repoID int64, isPull bool) ([]*Issue, error) {
+	issues := make([]*Issue, 0)
+
+	err := db.GetEngine(ctx).
+		Table("issue").
+		Where("repo_id = ?", repoID).
+		And("is_pull = ?", isPull).
+		And("pin_order > 0").
+		OrderBy("pin_order").
+		Find(&issues)
+	if err != nil {
+		return nil, err
+	}
+
+	err = IssueList(issues).LoadAttributes()
+	if err != nil {
+		return nil, err
+	}
+
+	return issues, nil
+}
+
+// IsNewPinnedAllowed returns if a new Issue or Pull request can be pinned
+func IsNewPinAllowed(ctx context.Context, repoID int64, isPull bool) (bool, error) {
+	var maxPin int
+	_, err := db.GetEngine(ctx).SQL("SELECT MAX(pin_order) FROM issue WHERE repo_id = ? AND is_pull = ?", repoID, isPull).Get(&maxPin)
+	if err != nil {
+		return false, err
+	}
+
+	return maxPin < setting.Repository.Issue.MaxPinned, nil
+}
diff --git a/models/migrations/migrations.go b/models/migrations/migrations.go
index 49bc0be4e50f..231c93cc74bb 100644
--- a/models/migrations/migrations.go
+++ b/models/migrations/migrations.go
@@ -493,6 +493,8 @@ var migrations = []Migration{
 	NewMigration("Add is_internal column to package", v1_20.AddIsInternalColumnToPackage),
 	// v257 -> v258
 	NewMigration("Add Actions Artifact table", v1_20.CreateActionArtifactTable),
+	// v258 -> 259
+	NewMigration("Add PinOrder Column", v1_20.AddPinOrderToIssue),
 }
 
 // GetCurrentDBVersion returns the current db version
diff --git a/models/migrations/v1_20/v258.go b/models/migrations/v1_20/v258.go
new file mode 100644
index 000000000000..47174ce8051a
--- /dev/null
+++ b/models/migrations/v1_20/v258.go
@@ -0,0 +1,16 @@
+// Copyright 2023 The Gitea Authors. All rights reserved.
+// SPDX-License-Identifier: MIT
+
+package v1_20 //nolint
+
+import (
+	"xorm.io/xorm"
+)
+
+func AddPinOrderToIssue(x *xorm.Engine) error {
+	type Issue struct {
+		PinOrder int `xorm:"DEFAULT 0"`
+	}
+
+	return x.Sync(new(Issue))
+}
diff --git a/modules/setting/repository.go b/modules/setting/repository.go
index 5520c992b969..406068b59dd5 100644
--- a/modules/setting/repository.go
+++ b/modules/setting/repository.go
@@ -90,6 +90,7 @@ var (
 		// Issue Setting
 		Issue struct {
 			LockReasons []string
+			MaxPinned   int
 		} `ini:"repository.issue"`
 
 		Release struct {
@@ -227,8 +228,10 @@ var (
 		// Issue settings
 		Issue: struct {
 			LockReasons []string
+			MaxPinned   int
 		}{
 			LockReasons: strings.Split("Too heated,Off-topic,Spam,Resolved", ","),
+			MaxPinned:   3,
 		},
 
 		Release: struct {
diff --git a/modules/structs/issue.go b/modules/structs/issue.go
index 04e169df8419..a9fb6c6e797b 100644
--- a/modules/structs/issue.go
+++ b/modules/structs/issue.go
@@ -75,6 +75,8 @@ type Issue struct {
 
 	PullRequest *PullRequestMeta `json:"pull_request"`
 	Repo        *RepositoryMeta  `json:"repository"`
+
+	PinOrder int `json:"pin_order"`
 }
 
 // CreateIssueOption options to create one issue
diff --git a/modules/structs/pull.go b/modules/structs/pull.go
index a4a6f60b0568..05a8d596338b 100644
--- a/modules/structs/pull.go
+++ b/modules/structs/pull.go
@@ -49,6 +49,8 @@ type PullRequest struct {
 	Updated *time.Time `json:"updated_at"`
 	// swagger:strfmt date-time
 	Closed *time.Time `json:"closed_at"`
+
+	PinOrder int `json:"pin_order"`
 }
 
 // PRBranchInfo information about a branch
diff --git a/modules/structs/repo.go b/modules/structs/repo.go
index 01239188c2cd..fc4ed03de553 100644
--- a/modules/structs/repo.go
+++ b/modules/structs/repo.go
@@ -374,3 +374,9 @@ type RepoTransfer struct {
 	Recipient *User   `json:"recipient"`
 	Teams     []*Team `json:"teams"`
 }
+
+// NewIssuePinsAllowed represents an API response that says if new Issue Pins are allowed
+type NewIssuePinsAllowed struct {
+	Issues       bool `json:"issues"`
+	PullRequests bool `json:"pull_requests"`
+}
diff --git a/options/locale/locale_en-US.ini b/options/locale/locale_en-US.ini
index 458c99f7fe97..1026a13e3338 100644
--- a/options/locale/locale_en-US.ini
+++ b/options/locale/locale_en-US.ini
@@ -115,6 +115,9 @@ unknown = Unknown
 
 rss_feed = RSS Feed
 
+pin = Pin
+unpin = Unpin
+
 artifacts = Artifacts
 
 concept_system_global = Global
@@ -1482,6 +1485,10 @@ issues.attachment.open_tab = `Click to see "%s" in a new tab`
 issues.attachment.download = `Click to download "%s"`
 issues.subscribe = Subscribe
 issues.unsubscribe = Unsubscribe
+issues.unpin_issue = Unpin Issue
+issues.max_pinned = "You can't pin more issues"
+issues.pin_comment = "pinned this %s"
+issues.unpin_comment = "unpinned this %s"
 issues.lock = Lock conversation
 issues.unlock = Unlock conversation
 issues.lock.unknown_reason = Cannot lock an issue with an unknown reason.
diff --git a/routers/api/v1/api.go b/routers/api/v1/api.go
index 53c58c4b9b6f..fccfc5792ca7 100644
--- a/routers/api/v1/api.go
+++ b/routers/api/v1/api.go
@@ -967,6 +967,7 @@ func Routes(ctx gocontext.Context) *web.Route {
 				m.Group("/issues", func() {
 					m.Combo("").Get(repo.ListIssues).
 						Post(reqToken(auth_model.AccessTokenScopeRepo), mustNotBeArchived, bind(api.CreateIssueOption{}), repo.CreateIssue)
+					m.Get("/pinned", repo.ListPinnedIssues)
 					m.Group("/comments", func() {
 						m.Get("", repo.ListRepoIssueComments)
 						m.Group("/{id}", func() {
@@ -1047,6 +1048,12 @@ func Routes(ctx gocontext.Context) *web.Route {
 							Get(repo.GetIssueBlocks).
 							Post(reqToken(auth_model.AccessTokenScopeRepo), bind(api.IssueMeta{}), repo.CreateIssueBlocking).
 							Delete(reqToken(auth_model.AccessTokenScopeRepo), bind(api.IssueMeta{}), repo.RemoveIssueBlocking)
+						m.Group("/pin", func() {
+							m.Combo("").
+								Post(reqToken(auth_model.AccessTokenScopeRepo), reqAdmin(), repo.PinIssue).
+								Delete(reqToken(auth_model.AccessTokenScopeRepo), reqAdmin(), repo.UnpinIssue)
+							m.Patch("/{position}", reqToken(auth_model.AccessTokenScopeRepo), reqAdmin(), repo.MoveIssuePin)
+						})
 					})
 				}, mustEnableIssuesOrPulls)
 				m.Group("/labels", func() {
@@ -1109,6 +1116,7 @@ func Routes(ctx gocontext.Context) *web.Route {
 				m.Group("/pulls", func() {
 					m.Combo("").Get(repo.ListPullRequests).
 						Post(reqToken(auth_model.AccessTokenScopeRepo), mustNotBeArchived, bind(api.CreatePullRequestOption{}), repo.CreatePullRequest)
+					m.Get("/pinned", repo.ListPinnedPullRequests)
 					m.Group("/{index}", func() {
 						m.Combo("").Get(repo.GetPullRequest).
 							Patch(reqToken(auth_model.AccessTokenScopeRepo), bind(api.EditPullRequestOption{}), repo.EditPullRequest)
@@ -1186,6 +1194,7 @@ func Routes(ctx gocontext.Context) *web.Route {
 				m.Get("/issue_config/validate", context.ReferencesGitRepo(), repo.ValidateIssueConfig)
 				m.Get("/languages", reqRepoReader(unit.TypeCode), repo.GetLanguages)
 				m.Get("/activities/feeds", repo.ListRepoActivityFeeds)
+				m.Get("/new_pin_allowed", repo.AreNewIssuePinsAllowed)
 			}, repoAssignment())
 		})
 
diff --git a/routers/api/v1/repo/issue_pin.go b/routers/api/v1/repo/issue_pin.go
new file mode 100644
index 000000000000..c96ede45f51b
--- /dev/null
+++ b/routers/api/v1/repo/issue_pin.go
@@ -0,0 +1,301 @@
+// Copyright 2023 The Gitea Authors. All rights reserved.
+// SPDX-License-Identifier: MIT
+
+package repo
+
+import (
+	"net/http"
+
+	issues_model "code.gitea.io/gitea/models/issues"
+	"code.gitea.io/gitea/modules/context"
+	api "code.gitea.io/gitea/modules/structs"
+	"code.gitea.io/gitea/services/convert"
+)
+
+// PinIssue pins a issue
+func PinIssue(ctx *context.APIContext) {
+	// swagger:operation POST /repos/{owner}/{repo}/issues/{index}/pin issue pinIssue
+	// ---
+	// summary: Pin an Issue
+	// parameters:
+	// - name: owner
+	//   in: path
+	//   description: owner of the repo
+	//   type: string
+	//   required: true
+	// - name: repo
+	//   in: path
+	//   description: name of the repo
+	//   type: string
+	//   required: true
+	// - name: index
+	//   in: path
+	//   description: index of issue to pin
+	//   type: integer
+	//   format: int64
+	//   required: true
+	// responses:
+	//   "204":
+	//     "$ref": "#/responses/empty"
+	//   "403":
+	//     "$ref": "#/responses/forbidden"
+	//   "404":
+	//     "$ref": "#/responses/notFound"
+	issue, err := issues_model.GetIssueByIndex(ctx.Repo.Repository.ID, ctx.ParamsInt64(":index"))
+	if err != nil {
+		if issues_model.IsErrIssueNotExist(err) {
+			ctx.NotFound()
+		} else {
+			ctx.Error(http.StatusInternalServerError, "GetIssueByIndex", err)
+		}
+		return
+	}
+
+	// If we don't do this, it will crash when trying to add the pin event to the comment history
+	err = issue.LoadRepo(ctx)
+	if err != nil {
+		ctx.Error(http.StatusInternalServerError, "LoadRepo", err)
+	}
+
+	err = issue.Pin(ctx, ctx.Doer)
+	if err != nil {
+		ctx.Error(http.StatusInternalServerError, "PinIssue", err)
+	}
+
+	ctx.Status(http.StatusNoContent)
+}
+
+// UnpinIssue unpins a Issue
+func UnpinIssue(ctx *context.APIContext) {
+	// swagger:operation DELETE /repos/{owner}/{repo}/issues/{index}/pin issue unpinIssue
+	// ---
+	// summary: Unpin an Issue
+	// parameters:
+	// - name: owner
+	//   in: path
+	//   description: owner of the repo
+	//   type: string
+	//   required: true
+	// - name: repo
+	//   in: path
+	//   description: name of the repo
+	//   type: string
+	//   required: true
+	// - name: index
+	//   in: path
+	//   description: index of issue to unpin
+	//   type: integer
+	//   format: int64
+	//   required: true
+	// responses:
+	//   "204":
+	//     "$ref": "#/responses/empty"
+	//   "403":
+	//     "$ref": "#/responses/forbidden"
+	//   "404":
+	//     "$ref": "#/responses/notFound"
+	issue, err := issues_model.GetIssueByIndex(ctx.Repo.Repository.ID, ctx.ParamsInt64(":index"))
+	if err != nil {
+		if issues_model.IsErrIssueNotExist(err) {
+			ctx.NotFound()
+		} else {
+			ctx.Error(http.StatusInternalServerError, "GetIssueByIndex", err)
+		}
+		return
+	}
+
+	// If we don't do this, it will crash when trying to add the unpin event to the comment history
+	err = issue.LoadRepo(ctx)
+	if err != nil {
+		ctx.Error(http.StatusInternalServerError, "LoadRepo", err)
+	}
+
+	err = issue.Unpin(ctx, ctx.Doer)
+	if err != nil {
+		ctx.Error(http.StatusInternalServerError, "UnpinIssue", err)
+	}
+
+	ctx.Status(http.StatusNoContent)
+}
+
+// MoveIssuePin moves a pinned Issue to a new Position
+func MoveIssuePin(ctx *context.APIContext) {
+	// swagger:operation PATCH /repos/{owner}/{repo}/issues/{index}/pin/{position} issue moveIssuePin
+	// ---
+	// summary: Moves the Pin to the given Position
+	// parameters:
+	// - name: owner
+	//   in: path
+	//   description: owner of the repo
+	//   type: string
+	//   required: true
+	// - name: repo
+	//   in: path
+	//   description: name of the repo
+	//   type: string
+	//   required: true
+	// - name: index
+	//   in: path
+	//   description: index of issue
+	//   type: integer
+	//   format: int64
+	//   required: true
+	// - name: position
+	//   in: path
+	//   description: the new position
+	//   type: integer
+	//   format: int64
+	//   required: true
+	// responses:
+	//   "204":
+	//     "$ref": "#/responses/empty"
+	//   "403":
+	//     "$ref": "#/responses/forbidden"
+	//   "404":
+	//     "$ref": "#/responses/notFound"
+	issue, err := issues_model.GetIssueByIndex(ctx.Repo.Repository.ID, ctx.ParamsInt64(":index"))
+	if err != nil {
+		if issues_model.IsErrIssueNotExist(err) {
+			ctx.NotFound()
+		} else {
+			ctx.Error(http.StatusInternalServerError, "GetIssueByIndex", err)
+		}
+		return
+	}
+
+	err = issue.MovePin(ctx, int(ctx.ParamsInt64(":position")))
+	if err != nil {
+		ctx.Error(http.StatusInternalServerError, "MovePin", err)
+	}
+
+	ctx.Status(http.StatusNoContent)
+}
+
+// ListPinnedIssues returns a list of all pinned Issues
+func ListPinnedIssues(ctx *context.APIContext) {
+	// swagger:operation GET /repos/{owner}/{repo}/issues/pinned repository repoListPinnedIssues
+	// ---
+	// summary: List a repo's pinned issues
+	// produces:
+	// - application/json
+	// parameters:
+	// - name: owner
+	//   in: path
+	//   description: owner of the repo
+	//   type: string
+	//   required: true
+	// - name: repo
+	//   in: path
+	//   description: name of the repo
+	//   type: string
+	//   required: true
+	// responses:
+	//   "200":
+	//     "$ref": "#/responses/IssueList"
+	issues, err := issues_model.GetPinnedIssues(ctx, ctx.Repo.Repository.ID, false)
+
+	if err == nil {
+		ctx.JSON(http.StatusOK, convert.ToAPIIssueList(ctx, issues))
+	} else {
+		ctx.Error(http.StatusInternalServerError, "LoadPinnedIssues", err)
+	}
+}
+
+// ListPinnedPullRequests returns a list of all pinned PRs
+func ListPinnedPullRequests(ctx *context.APIContext) {
+	// swagger:operation GET /repos/{owner}/{repo}/pulls/pinned repository repoListPinnedPullRequests
+	// ---
+	// summary: List a repo's pinned pull requests
+	// produces:
+	// - application/json
+	// parameters:
+	// - name: owner
+	//   in: path
+	//   description: owner of the repo
+	//   type: string
+	//   required: true
+	// - name: repo
+	//   in: path
+	//   description: name of the repo
+	//   type: string
+	//   required: true
+	// responses:
+	//   "200":
+	//     "$ref": "#/responses/PullRequestList"
+	issues, err := issues_model.GetPinnedIssues(ctx, ctx.Repo.Repository.ID, true)
+	if err != nil {
+		ctx.Error(http.StatusInternalServerError, "LoadPinnedPullRequests", err)
+	}
+
+	apiPrs := make([]*api.PullRequest, len(issues))
+	for i, currentIssue := range issues {
+		pr, err := currentIssue.GetPullRequest()
+		if err != nil {
+			ctx.Error(http.StatusInternalServerError, "GetPullRequest", err)
+			return
+		}
+
+		if err = pr.LoadIssue(ctx); err != nil {
+			ctx.Error(http.StatusInternalServerError, "LoadIssue", err)
+			return
+		}
+
+		if err = pr.LoadAttributes(ctx); err != nil {
+			ctx.Error(http.StatusInternalServerError, "LoadAttributes", err)
+			return
+		}
+
+		if err = pr.LoadBaseRepo(ctx); err != nil {
+			ctx.Error(http.StatusInternalServerError, "LoadBaseRepo", err)
+			return
+		}
+
+		if err = pr.LoadHeadRepo(ctx); err != nil {
+			ctx.Error(http.StatusInternalServerError, "LoadHeadRepo", err)
+			return
+		}
+
+		apiPrs[i] = convert.ToAPIPullRequest(ctx, pr, ctx.Doer)
+	}
+
+	ctx.JSON(http.StatusOK, &apiPrs)
+}
+
+// AreNewIssuePinsAllowed returns if new issues pins are allowed
+func AreNewIssuePinsAllowed(ctx *context.APIContext) {
+	// swagger:operation GET /repos/{owner}/{repo}/new_pin_allowed repository repoNewPinAllowed
+	// ---
+	// summary: Returns if new Issue Pins are allowed
+	// produces:
+	// - application/json
+	// parameters:
+	// - name: owner
+	//   in: path
+	//   description: owner of the repo
+	//   type: string
+	//   required: true
+	// - name: repo
+	//   in: path
+	//   description: name of the repo
+	//   type: string
+	//   required: true
+	// responses:
+	//   "200":
+	//     "$ref": "#/responses/RepoNewIssuePinsAllowed"
+	pinsAllowed := api.NewIssuePinsAllowed{}
+	var err error
+
+	pinsAllowed.Issues, err = issues_model.IsNewPinAllowed(ctx, ctx.Repo.Repository.ID, false)
+	if err != nil {
+		ctx.Error(http.StatusInternalServerError, "IsNewIssuePinAllowed", err)
+		return
+	}
+
+	pinsAllowed.PullRequests, err = issues_model.IsNewPinAllowed(ctx, ctx.Repo.Repository.ID, true)
+	if err != nil {
+		ctx.Error(http.StatusInternalServerError, "IsNewPullRequestPinAllowed", err)
+		return
+	}
+
+	ctx.JSON(http.StatusOK, pinsAllowed)
+}
diff --git a/routers/api/v1/swagger/repo.go b/routers/api/v1/swagger/repo.go
index e0418e99dc44..10056ac8cbb8 100644
--- a/routers/api/v1/swagger/repo.go
+++ b/routers/api/v1/swagger/repo.go
@@ -400,3 +400,10 @@ type swaggerRepoIssueConfigValidation struct {
 	// in:body
 	Body api.IssueConfigValidation `json:"body"`
 }
+
+// RepoNewIssuePinsAllowed
+// swagger:response RepoNewIssuePinsAllowed
+type swaggerRepoNewIssuePinsAllowed struct {
+	// in:body
+	Body api.NewIssuePinsAllowed `json:"body"`
+}
diff --git a/routers/web/repo/issue.go b/routers/web/repo/issue.go
index 1511716c1e50..1448b772bce0 100644
--- a/routers/web/repo/issue.go
+++ b/routers/web/repo/issue.go
@@ -388,6 +388,14 @@ func issues(ctx *context.Context, milestoneID, projectID int64, isPullOption uti
 		return
 	}
 
+	pinned, err := issues_model.GetPinnedIssues(ctx, repo.ID, isPullOption.IsTrue())
+	if err != nil {
+		ctx.ServerError("GetPinnedIssues", err)
+		return
+	}
+
+	ctx.Data["PinnedIssues"] = pinned
+	ctx.Data["IsRepoAdmin"] = ctx.IsSigned && (ctx.Repo.IsAdmin() || ctx.Doer.IsAdmin)
 	ctx.Data["IssueStats"] = issueStats
 	ctx.Data["SelLabelIDs"] = labelIDs
 	ctx.Data["SelectLabels"] = selectLabels
@@ -1854,6 +1862,17 @@ func ViewIssue(ctx *context.Context) {
 		return
 	}
 
+	var pinAllowed bool
+	if !issue.IsPinned() {
+		pinAllowed, err = issues_model.IsNewPinAllowed(ctx, issue.RepoID, issue.IsPull)
+		if err != nil {
+			ctx.ServerError("IsNewPinAllowed", err)
+			return
+		}
+	} else {
+		pinAllowed = true
+	}
+
 	ctx.Data["Participants"] = participants
 	ctx.Data["NumParticipants"] = len(participants)
 	ctx.Data["Issue"] = issue
@@ -1865,6 +1884,8 @@ func ViewIssue(ctx *context.Context) {
 	ctx.Data["IsRepoAdmin"] = ctx.IsSigned && (ctx.Repo.IsAdmin() || ctx.Doer.IsAdmin)
 	ctx.Data["LockReasons"] = setting.Repository.Issue.LockReasons
 	ctx.Data["RefEndName"] = git.RefEndName(issue.Ref)
+	ctx.Data["NewPinAllowed"] = pinAllowed
+	ctx.Data["PinEnabled"] = setting.Repository.Issue.MaxPinned != 0
 
 	var hiddenCommentTypes *big.Int
 	if ctx.IsSigned {
diff --git a/routers/web/repo/issue_pin.go b/routers/web/repo/issue_pin.go
new file mode 100644
index 000000000000..13f2d02fe845
--- /dev/null
+++ b/routers/web/repo/issue_pin.go
@@ -0,0 +1,88 @@
+// Copyright 2023 The Gitea Authors. All rights reserved.
+// SPDX-License-Identifier: MIT
+
+package repo
+
+import (
+	"net/http"
+
+	issues_model "code.gitea.io/gitea/models/issues"
+	"code.gitea.io/gitea/modules/context"
+	"code.gitea.io/gitea/modules/json"
+)
+
+// IssuePinOrUnpin pin or unpin a Issue
+func IssuePinOrUnpin(ctx *context.Context) {
+	issue := GetActionIssue(ctx)
+
+	// If we don't do this, it will crash when trying to add the pin event to the comment history
+	err := issue.LoadRepo(ctx)
+	if err != nil {
+		ctx.Status(http.StatusInternalServerError)
+		return
+	}
+
+	err = issue.PinOrUnpin(ctx, ctx.Doer)
+	if err != nil {
+		ctx.Status(http.StatusInternalServerError)
+		return
+	}
+
+	ctx.Redirect(issue.Link())
+}
+
+// IssueUnpin unpins a Issue
+func IssueUnpin(ctx *context.Context) {
+	issue, err := issues_model.GetIssueByIndex(ctx.Repo.Repository.ID, ctx.ParamsInt64(":id"))
+	if err != nil {
+		ctx.Status(http.StatusNoContent)
+		return
+	}
+
+	// If we don't do this, it will crash when trying to add the pin event to the comment history
+	err = issue.LoadRepo(ctx)
+	if err != nil {
+		ctx.Status(http.StatusInternalServerError)
+		return
+	}
+
+	err = issue.Unpin(ctx, ctx.Doer)
+	if err != nil {
+		ctx.Status(http.StatusInternalServerError)
+	}
+
+	ctx.Status(http.StatusNoContent)
+}
+
+// IssuePinMove moves a pinned Issue
+func IssuePinMove(ctx *context.Context) {
+	if ctx.Doer == nil {
+		ctx.JSON(http.StatusForbidden, "Only signed in users are allowed to perform this action.")
+		return
+	}
+
+	type movePinIssueForm struct {
+		ID       int64 `json:"id"`
+		Position int   `json:"position"`
+	}
+
+	form := &movePinIssueForm{}
+	if err := json.NewDecoder(ctx.Req.Body).Decode(&form); err != nil {
+		ctx.Status(http.StatusInternalServerError)
+		return
+	}
+
+	issue, err := issues_model.GetIssueByID(ctx, form.ID)
+	if err != nil {
+		ctx.Status(http.StatusInternalServerError)
+		return
+	}
+
+	err = issue.MovePin(ctx, form.Position)
+	if err != nil {
+		ctx.Status(http.StatusInternalServerError)
+		return
+	}
+
+	ctx.Status(http.StatusNoContent)
+}
diff --git a/routers/web/web.go b/routers/web/web.go
index 395fc9425f22..a38638c48340 100644
--- a/routers/web/web.go
+++ b/routers/web/web.go
@@ -987,6 +987,7 @@ func registerRoutes(m *web.Route) {
 				m.Post("/deadline", web.Bind(structs.EditDeadlineOption{}), repo.UpdateIssueDeadline)
 				m.Post("/watch", repo.IssueWatch)
 				m.Post("/ref", repo.UpdateIssueRef)
+				m.Post("/pin", reqRepoAdmin, repo.IssuePinOrUnpin)
 				m.Post("/viewed-files", repo.UpdateViewedFiles)
 				m.Group("/dependency", func() {
 					m.Post("/add", repo.AddDependency)
@@ -1024,6 +1025,8 @@ func registerRoutes(m *web.Route) {
 			m.Post("/resolve_conversation", reqRepoIssuesOrPullsReader, repo.UpdateResolveConversation)
 			m.Post("/attachments", repo.UploadIssueAttachment)
 			m.Post("/attachments/remove", repo.DeleteAttachment)
+			m.Delete("/unpin/{id}", reqRepoAdmin, repo.IssueUnpin)
+			m.Post("/pin_move", reqRepoAdmin, repo.IssuePinMove)
 		}, context.RepoMustNotBeArchived())
 		m.Group("/comments/{id}", func() {
 			m.Post("", repo.UpdateCommentContent)
diff --git a/services/convert/issue.go b/services/convert/issue.go
index 3d1b21c6bf86..bcb1618e8faf 100644
--- a/services/convert/issue.go
+++ b/services/convert/issue.go
@@ -47,6 +47,7 @@ func ToAPIIssue(ctx context.Context, issue *issues_model.Issue) *api.Issue {
 		Comments:    issue.NumComments,
 		Created:     issue.CreatedUnix.AsTime(),
 		Updated:     issue.UpdatedUnix.AsTime(),
+		PinOrder:    issue.PinOrder,
 	}
 
 	if issue.Repo != nil {
diff --git a/services/convert/pull.go b/services/convert/pull.go
index 598187ca6e0f..1ac0f4e96f1e 100644
--- a/services/convert/pull.go
+++ b/services/convert/pull.go
@@ -72,6 +72,7 @@ func ToAPIPullRequest(ctx context.Context, pr *issues_model.PullRequest, doer *u
 		Deadline:  apiIssue.Deadline,
 		Created:   pr.Issue.CreatedUnix.AsTimePtr(),
 		Updated:   pr.Issue.UpdatedUnix.AsTimePtr(),
+		PinOrder:  apiIssue.PinOrder,
 
 		AllowMaintainerEdit: pr.AllowMaintainerEdit,
 
diff --git a/services/issue/issue.go b/services/issue/issue.go
index d4f827e99af5..06da47152c7d 100644
--- a/services/issue/issue.go
+++ b/services/issue/issue.go
@@ -153,6 +153,13 @@ func DeleteIssue(ctx context.Context, doer *user_model.User, gitRepo *git.Reposi
 		}
 	}
 
+	// If the Issue is pinned, we should unpin it before deletion to avoid problems with other pinned Issues
+	if issue.IsPinned() {
+		if err := issue.Unpin(ctx, doer); err != nil {
+			return err
+		}
+	}
+
 	notification.NotifyDeleteIssue(ctx, doer, issue)
 
 	return nil
diff --git a/templates/repo/issue/list.tmpl b/templates/repo/issue/list.tmpl
index 7c2f73ca5929..dab6652d2172 100644
--- a/templates/repo/issue/list.tmpl
+++ b/templates/repo/issue/list.tmpl
@@ -2,6 +2,70 @@
 <div role="main" aria-label="{{.Title}}" class="page-content repository issue-list">
 	{{template "repo/header" .}}
 	<div class="ui container">
+
+	{{if .PinnedIssues}}
+		<div id="issue-pins" {{if .IsRepoAdmin}}data-is-repo-admin{{end}}>
+			{{range .PinnedIssues}}
+				<div class="pinned-issue-card gt-word-break" data-move-url="{{$.Link}}/pin_move" data-issue-id="{{.ID}}">
+					{{if eq $.Project.CardType 1}}
+						<div class="card-attachment-images">
+							{{range (index $.issuesAttachmentMap .ID)}}
+								<img src="{{.DownloadURL}}" alt="{{.Name}}">
+							{{end}}
+						</div>
+					{{end}}
+					<div class="content gt-p-0">
+						<div class="header gt-df gt-items-start">
+							<div class="pinned-issue-icon">
+								{{template "shared/issueicon" .}}
+							</div>
+							<a class="pinned-issue-title muted issue-title" href="{{.Link}}">{{.Title | RenderEmoji $.Context | RenderCodeBlock}}</a>
+							{{if $.IsRepoAdmin}}
+								<a role="button" class="pinned-issue-unpin muted gt-df gt-ac" data-tooltip-content={{$.locale.Tr "repo.issues.unpin_issue"}} data-issue-id="{{.ID}}" data-unpin-url="{{$.Link}}/unpin/{{.ID}}">
+									{{svg "octicon-x" 16}}
+								</a>
+							{{end}}
+						</div>
+						<div class="meta gt-my-2">
+							<span class="text light grey">
+								#{{.Index}}
+								{{$timeStr := TimeSinceUnix .GetLastEventTimestamp $.locale}}
+								{{if .OriginalAuthor}}
+									{{$.locale.Tr .GetLastEventLabelFake $timeStr (.OriginalAuthor|Escape) | Safe}}
+								{{else if gt .Poster.ID 0}}
+									{{$.locale.Tr .GetLastEventLabel $timeStr (.Poster.HomeLink|Escape) (.Poster.GetDisplayName | Escape) | Safe}}
+								{{else}}
+									{{$.locale.Tr .GetLastEventLabelFake $timeStr (.Poster.GetDisplayName | Escape) | Safe}}
+								{{end}}
+							</span>
+						</div>
+						{{- if .MilestoneID}}
+						<div class="meta gt-my-2">
+							<a class="milestone" href="{{$.RepoLink}}/milestone/{{.MilestoneID}}">
+								{{svg "octicon-milestone" 16 "gt-mr-2 gt-vm"}}
+								<span class="gt-vm">{{.Milestone.Name}}</span>
+							</a>
+						</div>
+						{{- end}}
+					</div>
+
+					{{if or .Labels .Assignees}}
+					<div class="extra content labels-list gt-p-0 gt-pt-2">
+						{{range .Labels}}
+							<a href="{{$.RepoLink}}/issues?labels={{.ID}}">{{RenderLabel $.Context .}}</a>
+						{{end}}
+						<div class="right floated">
+							{{range .Assignees}}
+								<a href="{{.HomeLink}}" data-tooltip-content="{{$.locale.Tr "repo.projects.column.assigned_to"}} {{.Name}}">{{avatar $.Context . 28 "mini gt-mr-3"}}</a>
+							{{end}}
+						</div>
+					</div>
+					{{end}}
+				</div>
+			{{end}}
+		</div>
+	{{end}}
+
 		<div class="list-header">
 			{{template "repo/issue/navbar" .}}
 			{{template "repo/issue/search" .}}
diff --git a/templates/repo/issue/view_content/comments.tmpl b/templates/repo/issue/view_content/comments.tmpl
index b65ebc68a24f..5091201ddecc 100644
--- a/templates/repo/issue/view_content/comments.tmpl
+++ b/templates/repo/issue/view_content/comments.tmpl
@@ -11,7 +11,7 @@
 		26 = DELETE_TIME_MANUAL, 27 = REVIEW_REQUEST, 28 = MERGE_PULL_REQUEST,
 		29 = PULL_PUSH_EVENT, 30 = PROJECT_CHANGED, 31 = PROJECT_BOARD_CHANGED
 		32 = DISMISSED_REVIEW, 33 = COMMENT_TYPE_CHANGE_ISSUE_REF, 34 = PR_SCHEDULE_TO_AUTO_MERGE,
-		35 = CANCEL_SCHEDULED_AUTO_MERGE_PR -->
+		35 = CANCEL_SCHEDULED_AUTO_MERGE_PR, 36 = PIN_ISSUE, 37 = UNPIN_ISSUE -->
 		{{if eq .Type 0}}
 			<div class="timeline-item comment" id="{{.HashTag}}">
 			{{if .OriginalAuthor}}
@@ -835,6 +835,16 @@
 					{{else}}{{$.locale.Tr "repo.pulls.auto_merge_canceled_schedule_comment" $createdStr | Safe}}{{end}}
 				</span>
 			</div>
+		{{else if or (eq .Type 36) (eq .Type 37)}}
+			<div class="timeline-item event" id="{{.HashTag}}">
+				<span class="badge">{{svg "octicon-pin" 16}}</span>
+				{{template "shared/user/avatarlink" dict "Context" $.Context "user" .Poster}}
+				<span class="text grey muted-links">
+					{{template "shared/user/authorlink" .Poster}}
+					{{if eq .Type 36}}{{$.locale.Tr "repo.issues.pin_comment" $createdStr | Safe}}
+					{{else}}{{$.locale.Tr "repo.issues.unpin_comment" $createdStr | Safe}}{{end}}
+				</span>
+			</div>
 		{{end}}
 	{{end}}
 {{end}}
diff --git a/templates/repo/issue/view_content/sidebar.tmpl b/templates/repo/issue/view_content/sidebar.tmpl
index c8e65d0900b5..60d2f4a5613d 100644
--- a/templates/repo/issue/view_content/sidebar.tmpl
+++ b/templates/repo/issue/view_content/sidebar.tmpl
@@ -530,17 +530,31 @@
 
 		{{if and .IsRepoAdmin (not .Repository.IsArchived)}}
 			<div class="ui divider"></div>
-			<div class="ui watching">
-				<button class="fluid ui show-modal button {{if .Issue.IsLocked}} negative {{end}}" data-modal="#lock">
-					{{if .Issue.IsLocked}}
-						{{svg "octicon-key"}}
-						{{.locale.Tr "repo.issues.unlock"}}
-					{{else}}
-						{{svg "octicon-lock"}}
-						{{.locale.Tr "repo.issues.lock"}}
-					{{end}}
-				</button>
-			</div>
+
+			{{if or .PinEnabled .Issue.IsPinned}}
+				<form class="gt-mt-2" method="POST" {{if $.NewPinAllowed}}action="{{.Issue.Link}}/pin"{{else}}data-tooltip-content="{{.locale.Tr "repo.issues.max_pinned"}}"{{end}}>
+					{{$.CsrfTokenHtml}}
+					<button class="fluid ui button gt-df gt-jc {{if not $.NewPinAllowed}}disabled{{end}}">
+						{{if not .Issue.IsPinned}}
+							{{svg "octicon-pin" 16 "gt-mr-3"}}
+							{{.locale.Tr "pin"}}
+						{{else}}
+							{{svg "octicon-pin-slash" 16 "gt-mr-3"}}
+							{{.locale.Tr "unpin"}}
+						{{end}}
+					</button>
+				</form>
+			{{end}}
+
+			<button class="gt-mt-2 fluid ui show-modal button {{if .Issue.IsLocked}} negative {{end}}" data-modal="#lock">
+				{{if .Issue.IsLocked}}
+					{{svg "octicon-key"}}
+					{{.locale.Tr "repo.issues.unlock"}}
+				{{else}}
+					{{svg "octicon-lock"}}
+					{{.locale.Tr "repo.issues.lock"}}
+				{{end}}
+			</button>
 			<div class="ui tiny modal" id="lock">
 				<div class="header">
 					{{if .Issue.IsLocked}}
@@ -605,7 +619,7 @@
 					</form>
 				</div>
 			</div>
-			<button class="fluid ui show-modal button negative gt-mt-3" data-modal="#delete">
+			<button class="gt-mt-2 fluid ui show-modal button negative" data-modal="#delete">
 				{{svg "octicon-trash"}}
 				{{.locale.Tr "repo.issues.delete"}}
 			</button>
diff --git a/templates/swagger/v1_json.tmpl b/templates/swagger/v1_json.tmpl
index 03a65184c3e2..15043e465f90 100644
--- a/templates/swagger/v1_json.tmpl
+++ b/templates/swagger/v1_json.tmpl
@@ -6191,6 +6191,39 @@
         }
       }
     },
+    "/repos/{owner}/{repo}/issues/pinned": {
+      "get": {
+        "produces": [
+          "application/json"
+        ],
+        "tags": [
+          "repository"
+        ],
+        "summary": "List a repo's pinned issues",
+        "operationId": "repoListPinnedIssues",
+        "parameters": [
+          {
+            "type": "string",
+            "description": "owner of the repo",
+            "name": "owner",
+            "in": "path",
+            "required": true
+          },
+          {
+            "type": "string",
+            "description": "name of the repo",
+            "name": "repo",
+            "in": "path",
+            "required": true
+          }
+        ],
+        "responses": {
+          "200": {
+            "$ref": "#/responses/IssueList"
+          }
+        }
+      }
+    },
     "/repos/{owner}/{repo}/issues/{index}": {
       "get": {
         "produces": [
@@ -7419,6 +7452,144 @@
         }
       }
     },
+    "/repos/{owner}/{repo}/issues/{index}/pin": {
+      "post": {
+        "tags": [
+          "issue"
+        ],
+        "summary": "Pin an Issue",
+        "operationId": "pinIssue",
+        "parameters": [
+          {
+            "type": "string",
+            "description": "owner of the repo",
+            "name": "owner",
+            "in": "path",
+            "required": true
+          },
+          {
+            "type": "string",
+            "description": "name of the repo",
+            "name": "repo",
+            "in": "path",
+            "required": true
+          },
+          {
+            "type": "integer",
+            "format": "int64",
+            "description": "index of issue to pin",
+            "name": "index",
+            "in": "path",
+            "required": true
+          }
+        ],
+        "responses": {
+          "204": {
+            "$ref": "#/responses/empty"
+          },
+          "403": {
+            "$ref": "#/responses/forbidden"
+          },
+          "404": {
+            "$ref": "#/responses/notFound"
+          }
+        }
+      },
+      "delete": {
+        "tags": [
+          "issue"
+        ],
+        "summary": "Unpin an Issue",
+        "operationId": "unpinIssue",
+        "parameters": [
+          {
+            "type": "string",
+            "description": "owner of the repo",
+            "name": "owner",
+            "in": "path",
+            "required": true
+          },
+          {
+            "type": "string",
+            "description": "name of the repo",
+            "name": "repo",
+            "in": "path",
+            "required": true
+          },
+          {
+            "type": "integer",
+            "format": "int64",
+            "description": "index of issue to unpin",
+            "name": "index",
+            "in": "path",
+            "required": true
+          }
+        ],
+        "responses": {
+          "204": {
+            "$ref": "#/responses/empty"
+          },
+          "403": {
+            "$ref": "#/responses/forbidden"
+          },
+          "404": {
+            "$ref": "#/responses/notFound"
+          }
+        }
+      }
+    },
+    "/repos/{owner}/{repo}/issues/{index}/pin/{position}": {
+      "patch": {
+        "tags": [
+          "issue"
+        ],
+        "summary": "Moves the Pin to the given Position",
+        "operationId": "moveIssuePin",
+        "parameters": [
+          {
+            "type": "string",
+            "description": "owner of the repo",
+            "name": "owner",
+            "in": "path",
+            "required": true
+          },
+          {
+            "type": "string",
+            "description": "name of the repo",
+            "name": "repo",
+            "in": "path",
+            "required": true
+          },
+          {
+            "type": "integer",
+            "format": "int64",
+            "description": "index of issue",
+            "name": "index",
+            "in": "path",
+            "required": true
+          },
+          {
+            "type": "integer",
+            "format": "int64",
+            "description": "the new position",
+            "name": "position",
+            "in": "path",
+            "required": true
+          }
+        ],
+        "responses": {
+          "204": {
+            "$ref": "#/responses/empty"
+          },
+          "403": {
+            "$ref": "#/responses/forbidden"
+          },
+          "404": {
+            "$ref": "#/responses/notFound"
+          }
+        }
+      }
+    },
     "/repos/{owner}/{repo}/issues/{index}/reactions": {
       "get": {
         "consumes": [
@@ -9010,6 +9181,39 @@
         }
       }
     },
+    "/repos/{owner}/{repo}/new_pin_allowed": {
+      "get": {
+        "produces": [
+          "application/json"
+        ],
+        "tags": [
+          "repository"
+        ],
+        "summary": "Returns if new Issue Pins are allowed",
+        "operationId": "repoNewPinAllowed",
+        "parameters": [
+          {
+            "type": "string",
+            "description": "owner of the repo",
+            "name": "owner",
+            "in": "path",
+            "required": true
+          },
+          {
+            "type": "string",
+            "description": "name of the repo",
+            "name": "repo",
+            "in": "path",
+            "required": true
+          }
+        ],
+        "responses": {
+          "200": {
+            "$ref": "#/responses/RepoNewIssuePinsAllowed"
+          }
+        }
+      }
+    },
     "/repos/{owner}/{repo}/notifications": {
       "get": {
         "consumes": [
@@ -9302,6 +9506,39 @@
         }
       }
     },
+    "/repos/{owner}/{repo}/pulls/pinned": {
+      "get": {
+        "produces": [
+          "application/json"
+        ],
+        "tags": [
+          "repository"
+        ],
+        "summary": "List a repo's pinned pull requests",
+        "operationId": "repoListPinnedPullRequests",
+        "parameters": [
+          {
+            "type": "string",
+            "description": "owner of the repo",
+            "name": "owner",
+            "in": "path",
+            "required": true
+          },
+          {
+            "type": "string",
+            "description": "name of the repo",
+            "name": "repo",
+            "in": "path",
+            "required": true
+          }
+        ],
+        "responses": {
+          "200": {
+            "$ref": "#/responses/PullRequestList"
+          }
+        }
+      }
+    },
     "/repos/{owner}/{repo}/pulls/{index}": {
       "get": {
         "produces": [
@@ -18664,6 +18901,11 @@
           "format": "int64",
           "x-go-name": "OriginalAuthorID"
         },
+        "pin_order": {
+          "type": "integer",
+          "format": "int64",
+          "x-go-name": "PinOrder"
+        },
         "pull_request": {
           "$ref": "#/definitions/PullRequestMeta"
         },
@@ -19224,6 +19466,21 @@
       },
       "x-go-package": "code.gitea.io/gitea/modules/structs"
     },
+    "NewIssuePinsAllowed": {
+      "description": "NewIssuePinsAllowed represents an API response that says if new Issue Pins are allowed",
+      "type": "object",
+      "properties": {
+        "issues": {
+          "type": "boolean",
+          "x-go-name": "Issues"
+        },
+        "pull_requests": {
+          "type": "boolean",
+          "x-go-name": "PullRequests"
+        }
+      },
+      "x-go-package": "code.gitea.io/gitea/modules/structs"
+    },
     "NodeInfo": {
       "description": "NodeInfo contains standardized way of exposing metadata about a server running one of the distributed social networks",
       "type": "object",
@@ -19934,6 +20191,11 @@
           "type": "string",
           "x-go-name": "PatchURL"
         },
+        "pin_order": {
+          "type": "integer",
+          "format": "int64",
+          "x-go-name": "PinOrder"
+        },
         "requested_reviewers": {
           "type": "array",
           "items": {
@@ -22176,6 +22438,12 @@
         "$ref": "#/definitions/IssueConfigValidation"
       }
     },
+    "RepoNewIssuePinsAllowed": {
+      "description": "RepoNewIssuePinsAllowed",
+      "schema": {
+        "$ref": "#/definitions/NewIssuePinsAllowed"
+      }
+    },
     "Repository": {
       "description": "Repository",
       "schema": {
diff --git a/tests/integration/api_issue_pin_test.go b/tests/integration/api_issue_pin_test.go
new file mode 100644
index 000000000000..65be1d74f2d3
--- /dev/null
+++ b/tests/integration/api_issue_pin_test.go
@@ -0,0 +1,205 @@
+// Copyright 2023 The Gitea Authors. All rights reserved.
+// SPDX-License-Identifier: MIT
+
+package integration
+
+import (
+	"fmt"
+	"net/http"
+	"testing"
+
+	auth_model "code.gitea.io/gitea/models/auth"
+	issues_model "code.gitea.io/gitea/models/issues"
+	repo_model "code.gitea.io/gitea/models/repo"
+	"code.gitea.io/gitea/models/unittest"
+	user_model "code.gitea.io/gitea/models/user"
+	api "code.gitea.io/gitea/modules/structs"
+	"code.gitea.io/gitea/tests"
+
+	"github.com/stretchr/testify/assert"
+)
+
+func TestAPIPinIssue(t *testing.T) {
+	defer tests.PrepareTestEnv(t)()
+
+	assert.NoError(t, unittest.LoadFixtures())
+
+	repo := unittest.AssertExistsAndLoadBean(t, &repo_model.Repository{ID: 1})
+	issue := unittest.AssertExistsAndLoadBean(t, &issues_model.Issue{RepoID: repo.ID})
+	owner := unittest.AssertExistsAndLoadBean(t, &user_model.User{ID: repo.OwnerID})
+
+	session := loginUser(t, owner.Name)
+	token := getTokenForLoggedInUser(t, session, auth_model.AccessTokenScopeRepo)
+
+	// Pin the Issue
+	urlStr := fmt.Sprintf("/api/v1/repos/%s/%s/issues/%d/pin?token=%s",
+		repo.OwnerName, repo.Name, issue.Index, token)
+	req := NewRequest(t, "POST", urlStr)
+	MakeRequest(t, req, http.StatusNoContent)
+
+	// Check if the Issue is pinned
+	urlStr = fmt.Sprintf("/api/v1/repos/%s/%s/issues/%d", repo.OwnerName, repo.Name, issue.Index)
+	req = NewRequest(t, "GET", urlStr)
+	resp := MakeRequest(t, req, http.StatusOK)
+	var issueAPI api.Issue
+	DecodeJSON(t, resp, &issueAPI)
+	assert.Equal(t, 1, issueAPI.PinOrder)
+}
+
+func TestAPIUnpinIssue(t *testing.T) {
+	defer tests.PrepareTestEnv(t)()
+
+	assert.NoError(t, unittest.LoadFixtures())
+
+	repo := unittest.AssertExistsAndLoadBean(t, &repo_model.Repository{ID: 1})
+	issue := unittest.AssertExistsAndLoadBean(t, &issues_model.Issue{RepoID: repo.ID})
+	owner := unittest.AssertExistsAndLoadBean(t, &user_model.User{ID: repo.OwnerID})
+
+	session := loginUser(t, owner.Name)
+	token := getTokenForLoggedInUser(t, session, auth_model.AccessTokenScopeRepo)
+
+	// Pin the Issue
+	urlStr := fmt.Sprintf("/api/v1/repos/%s/%s/issues/%d/pin?token=%s",
+		repo.OwnerName, repo.Name, issue.Index, token)
+	req := NewRequest(t, "POST", urlStr)
+	MakeRequest(t, req, http.StatusNoContent)
+
+	// Check if the Issue is pinned
+	urlStr = fmt.Sprintf("/api/v1/repos/%s/%s/issues/%d", repo.OwnerName, repo.Name, issue.Index)
+	req = NewRequest(t, "GET", urlStr)
+	resp := MakeRequest(t, req, http.StatusOK)
+	var issueAPI api.Issue
+	DecodeJSON(t, resp, &issueAPI)
+	assert.Equal(t, 1, issueAPI.PinOrder)
+
+	// Unpin the Issue
+	urlStr = fmt.Sprintf("/api/v1/repos/%s/%s/issues/%d/pin?token=%s",
+		repo.OwnerName, repo.Name, issue.Index, token)
+	req = NewRequest(t, "DELETE", urlStr)
+	MakeRequest(t, req, http.StatusNoContent)
+
+	// Check if the Issue is no longer pinned
+	urlStr = fmt.Sprintf("/api/v1/repos/%s/%s/issues/%d", repo.OwnerName, repo.Name, issue.Index)
+	req = NewRequest(t, "GET", urlStr)
+	resp = MakeRequest(t, req, http.StatusOK)
+	DecodeJSON(t, resp, &issueAPI)
+	assert.Equal(t, 0, issueAPI.PinOrder)
+}
+
+func TestAPIMoveIssuePin(t *testing.T) {
+	defer tests.PrepareTestEnv(t)()
+
+	assert.NoError(t, unittest.LoadFixtures())
+
+	repo := unittest.AssertExistsAndLoadBean(t, &repo_model.Repository{ID: 1})
+	issue := unittest.AssertExistsAndLoadBean(t, &issues_model.Issue{RepoID: repo.ID})
+	issue2 := unittest.AssertExistsAndLoadBean(t, &issues_model.Issue{ID: 2, RepoID: repo.ID})
+	owner := unittest.AssertExistsAndLoadBean(t, &user_model.User{ID: repo.OwnerID})
+
+	session := loginUser(t, owner.Name)
+	token := getTokenForLoggedInUser(t, session, auth_model.AccessTokenScopeRepo)
+
+	// Pin the first Issue
+	urlStr := fmt.Sprintf("/api/v1/repos/%s/%s/issues/%d/pin?token=%s",
+		repo.OwnerName, repo.Name, issue.Index, token)
+	req := NewRequest(t, "POST", urlStr)
+	MakeRequest(t, req, http.StatusNoContent)
+
+	// Check if the first Issue is pinned at position 1
+	urlStr = fmt.Sprintf("/api/v1/repos/%s/%s/issues/%d", repo.OwnerName, repo.Name, issue.Index)
+	req = NewRequest(t, "GET", urlStr)
+	resp := MakeRequest(t, req, http.StatusOK)
+	var issueAPI api.Issue
+	DecodeJSON(t, resp, &issueAPI)
+	assert.Equal(t, 1, issueAPI.PinOrder)
+
+	// Pin the second Issue
+	urlStr = fmt.Sprintf("/api/v1/repos/%s/%s/issues/%d/pin?token=%s",
+		repo.OwnerName, repo.Name, issue2.Index, token)
+	req = NewRequest(t, "POST", urlStr)
+	MakeRequest(t, req, http.StatusNoContent)
+
+	// Move the first Issue to position 2
+	urlStr = fmt.Sprintf("/api/v1/repos/%s/%s/issues/%d/pin/2?token=%s",
+		repo.OwnerName, repo.Name, issue.Index, token)
+	req = NewRequest(t, "PATCH", urlStr)
+	MakeRequest(t, req, http.StatusNoContent)
+
+	// Check if the first Issue is pinned at position 2
+	urlStr = fmt.Sprintf("/api/v1/repos/%s/%s/issues/%d", repo.OwnerName, repo.Name, issue.Index)
+	req = NewRequest(t, "GET", urlStr)
+	resp = MakeRequest(t, req, http.StatusOK)
+	var issueAPI3 api.Issue
+	DecodeJSON(t, resp, &issueAPI3)
+	assert.Equal(t, 2, issueAPI3.PinOrder)
+
+	// Check if the second Issue is pinned at position 1
+	urlStr = fmt.Sprintf("/api/v1/repos/%s/%s/issues/%d", repo.OwnerName, repo.Name, issue2.Index)
+	req = NewRequest(t, "GET", urlStr)
+	resp = MakeRequest(t, req, http.StatusOK)
+	var issueAPI4 api.Issue
+	DecodeJSON(t, resp, &issueAPI4)
+	assert.Equal(t, 1, issueAPI4.PinOrder)
+}
+
+func TestAPIListPinnedIssues(t *testing.T) {
+	defer tests.PrepareTestEnv(t)()
+
+	assert.NoError(t, unittest.LoadFixtures())
+
+	repo := unittest.AssertExistsAndLoadBean(t, &repo_model.Repository{ID: 1})
+	issue := unittest.AssertExistsAndLoadBean(t, &issues_model.Issue{RepoID: repo.ID})
+	owner := unittest.AssertExistsAndLoadBean(t, &user_model.User{ID: repo.OwnerID})
+
+	session := loginUser(t, owner.Name)
+	token := getTokenForLoggedInUser(t, session, auth_model.AccessTokenScopeRepo)
+
+	// Pin the Issue
+	urlStr := fmt.Sprintf("/api/v1/repos/%s/%s/issues/%d/pin?token=%s",
+		repo.OwnerName, repo.Name, issue.Index, token)
+	req := NewRequest(t, "POST", urlStr)
+	MakeRequest(t, req, http.StatusNoContent)
+
+	// Check if the Issue is in the List
+	urlStr = fmt.Sprintf("/api/v1/repos/%s/%s/issues/pinned", repo.OwnerName, repo.Name)
+	req = NewRequest(t, "GET", urlStr)
+	resp := MakeRequest(t, req, http.StatusOK)
+	var issueList []api.Issue
+	DecodeJSON(t, resp, &issueList)
+
+	assert.Equal(t, 1, len(issueList))
+	assert.Equal(t, issue.ID, issueList[0].ID)
+}
+
+func TestAPIListPinnedPullrequests(t *testing.T) {
+	defer tests.PrepareTestEnv(t)()
+
+	assert.NoError(t, unittest.LoadFixtures())
+
+	repo := unittest.AssertExistsAndLoadBean(t, &repo_model.Repository{ID: 1})
+
+	urlStr := fmt.Sprintf("/api/v1/repos/%s/%s/pulls/pinned", repo.OwnerName, repo.Name)
+	req := NewRequest(t, "GET", urlStr)
+	resp := MakeRequest(t, req, http.StatusOK)
+	var prList []api.PullRequest
+	DecodeJSON(t, resp, &prList)
+
+	assert.Equal(t, 0, len(prList))
+}
+
+func TestAPINewPinAllowed(t *testing.T) {
+	defer tests.PrepareTestEnv(t)()
+
+	repo := unittest.AssertExistsAndLoadBean(t, &repo_model.Repository{ID: 1})
+	owner := unittest.AssertExistsAndLoadBean(t, &user_model.User{ID: repo.OwnerID})
+
+	urlStr := fmt.Sprintf("/api/v1/repos/%s/%s/new_pin_allowed", owner.Name, repo.Name)
+	req := NewRequest(t, "GET", urlStr)
+	resp := MakeRequest(t, req, http.StatusOK)
+
+	var newPinsAllowed api.NewIssuePinsAllowed
+	DecodeJSON(t, resp, &newPinsAllowed)
+
+	assert.True(t, newPinsAllowed.Issues)
+	assert.True(t, newPinsAllowed.PullRequests)
+}
diff --git a/web_src/css/repo.css b/web_src/css/repo.css
index dbf9bf79bd56..069bf014b872 100644
--- a/web_src/css/repo.css
+++ b/web_src/css/repo.css
@@ -3387,3 +3387,37 @@ tbody.commit-list {
 .search-fullname {
   color: var(--color-text-light-2);
 }
+
+#issue-pins {
+  display: grid;
+  grid-template-columns: repeat(3, 1fr);
+  gap: 8px;
+  margin-bottom: 8px;
+}
+
+.pinned-issue-card {
+  border-radius: var(--border-radius);
+  padding: 8px 10px;
+  border: 1px solid var(--color-secondary);
+  background: var(--color-card);
+}
+
+.pinned-issue-card .meta a {
+  color: inherit;
+}
+
+.pinned-issue-card .meta a:hover {
+  color: var(--color-primary);
+}
+
+.pinned-issue-icon,
+.pinned-issue-unpin {
+  margin-top: 1px;
+  flex-shrink: 0;
+}
+
+.pinned-issue-title {
+  flex: 1;
+  font-size: 18px;
+  margin-left: 4px;
+}
diff --git a/web_src/js/features/repo-issue-list.js b/web_src/js/features/repo-issue-list.js
index af0e80af8109..cc50ec5f8817 100644
--- a/web_src/js/features/repo-issue-list.js
+++ b/web_src/js/features/repo-issue-list.js
@@ -2,6 +2,7 @@ import $ from 'jquery';
 import {updateIssuesMeta} from './repo-issue.js';
 import {toggleElem} from '../utils/dom.js';
 import {htmlEscape} from 'escape-goat';
+import {Sortable} from 'sortablejs';
 
 function initRepoIssueListCheckboxes() {
   const $issueSelectAll = $('.issue-checkbox-all');
@@ -119,8 +120,67 @@ function initRepoIssueListAuthorDropdown() {
   };
 }
 
+function initPinRemoveButton() {
+  for (const button of document.getElementsByClassName('pinned-issue-unpin')) {
+    button.addEventListener('click', async (event) => {
+      const el = event.currentTarget;
+      const id = Number(el.getAttribute('data-issue-id'));
+
+      // Send the unpin request
+      const response = await fetch(el.getAttribute('data-unpin-url'), {
+        method: 'delete',
+        headers: {
+          'X-Csrf-Token': window.config.csrfToken,
+          'Content-Type': 'application/json',
+        },
+      });
+      if (response.ok) {
+        // Delete the tooltip
+        el._tippy.destroy();
+        // Remove the Card
+        el.closest(`div.pinned-issue-card[data-issue-id="${id}"]`).remove();
+      }
+    });
+  }
+}
+
+async function pinMoveEnd(e) {
+  const url = e.item.getAttribute('data-move-url');
+  const id = Number(e.item.getAttribute('data-issue-id'));
+  await fetch(url, {
+    method: 'post',
+    body: JSON.stringify({id, position: e.newIndex + 1}),
+    headers: {
+      'X-Csrf-Token': window.config.csrfToken,
+      'Content-Type': 'application/json',
+    },
+  });
+}
+
+function initIssuePinSort() {
+  const pinDiv = document.getElementById('issue-pins');
+
+  if (pinDiv === null) return;
+
+  // If the User is not a Repo Admin, we don't need to proceed
+  if (!pinDiv.hasAttribute('data-is-repo-admin')) return;
+
+  initPinRemoveButton();
+
+  // If only one issue pinned, we don't need to make this Sortable
+  if (pinDiv.children.length < 2) return;
+
+  new Sortable(pinDiv, {
+    group: 'shared',
+    animation: 150,
+    ghostClass: 'card-ghost',
+    onEnd: pinMoveEnd,
+  });
+}
+
 export function initRepoIssueList() {
   if (!document.querySelectorAll('.page-content.repository.issue-list, .page-content.repository.milestone-issue-list').length) return;
   initRepoIssueListCheckboxes();
   initRepoIssueListAuthorDropdown();
+  initIssuePinSort();
 }