diff --git a/tools/github-manage/cmd/gm/main.go b/tools/github-manage/cmd/gm/main.go
index e40342c7eb..6c961e98c6 100644
--- a/tools/github-manage/cmd/gm/main.go
+++ b/tools/github-manage/cmd/gm/main.go
@@ -41,6 +41,8 @@ func main() {
 	rootCmd.AddCommand(projectCmd)
 	rootCmd.AddCommand(estimatedCmd)
 	rootCmd.AddCommand(sprintCmd)
+	rootCmd.AddCommand(milestoneCmd)
+	rootCmd.AddCommand(roadmapCmd)
 
 	// Test command to test SetCurrentSprint functionality
 	rootCmd.AddCommand(&cobra.Command{
diff --git a/tools/github-manage/cmd/gm/milestone.go b/tools/github-manage/cmd/gm/milestone.go
new file mode 100644
index 0000000000..b2343467e9
--- /dev/null
+++ b/tools/github-manage/cmd/gm/milestone.go
@@ -0,0 +1,397 @@
+package main
+
+import (
+	"fmt"
+	"sort"
+	"strings"
+
+	"github.com/spf13/cobra"
+
+	"fleetdm/gm/pkg/ghapi"
+)
+
+// milestoneCmd is the parent command for milestone-related operations.
+var milestoneCmd = &cobra.Command{
+	Use:   "milestone",
+	Short: "Milestone-related utilities",
+}
+
+var (
+	milestoneFormat        string
+	milestoneStripEmojis   bool
+	milestoneSummarySort   string
+	milestoneIncludeClosed bool
+	milestoneIgnoreProject string
+	milestoneFilterLabels  string
+)
+
+var milestoneReportCmd = &cobra.Command{
+	Use:   "report <milestone-name>",
+	Short: "Print a table of issues and their project statuses for a milestone",
+	Args:  cobra.ExactArgs(1),
+	RunE: func(cmd *cobra.Command, args []string) error {
+		milestoneName := args[0]
+
+		// Fetch issues in milestone (with titles)
+		msIssues, err := ghapi.GetIssuesByMilestoneWithTitles(milestoneName, 1000)
+		if err != nil || len(msIssues) == 0 {
+			// If milestone doesn't exist or has no issues, list available milestones
+			miles, lerr := ghapi.ListRepoMilestones(milestoneIncludeClosed)
+			if lerr != nil {
+				return fmt.Errorf("failed to find milestone '%s' and also failed to list milestones: %v", milestoneName, lerr)
+			}
+			format := strings.ToLower(strings.TrimSpace(milestoneFormat))
+			if format == "" {
+				format = "tsv"
+			}
+			// Helpful hint when filtering open-only yields none
+			var msg string
+			if len(miles) == 0 && !milestoneIncludeClosed {
+				msg = fmt.Sprintf("No open milestones found. Use --include-closed to include closed milestones. (Requested milestone: '%s')", milestoneName)
+			} else {
+				msg = fmt.Sprintf("No issues found for milestone '%s'. Available milestones:", milestoneName)
+			}
+			switch format {
+			case "tsv":
+				fmt.Println(msg)
+				fmt.Println(strings.Join([]string{"Title", "State"}, "\t"))
+				for _, m := range miles {
+					t := m.Title
+					if milestoneStripEmojis {
+						t = stripEmojis(t)
+					}
+					fmt.Println(strings.Join([]string{t, m.State}, "\t"))
+				}
+			case "md", "markdown":
+				fmt.Println(msg)
+				fmt.Printf("| %s |\n", strings.Join([]string{"Title", "State"}, " | "))
+				fmt.Printf("| %s |\n", strings.Join([]string{"---", "---"}, " | "))
+				for _, m := range miles {
+					t := m.Title
+					if milestoneStripEmojis {
+						t = stripEmojis(t)
+					}
+					fmt.Printf("| %s | %s |\n", t, m.State)
+				}
+			default:
+				return fmt.Errorf("unsupported --format %q (use: tsv or md)", milestoneFormat)
+			}
+			// Return error so callers can detect non-report condition
+			return fmt.Errorf("milestone '%s' not found or empty", milestoneName)
+		}
+		// Optional label filtering: require all specified labels to be present
+		if strings.TrimSpace(milestoneFilterLabels) != "" {
+			wantParts := strings.Split(milestoneFilterLabels, ",")
+			wants := make([]string, 0, len(wantParts))
+			for _, wp := range wantParts {
+				w := strings.ToLower(strings.TrimSpace(wp))
+				if w != "" {
+					wants = append(wants, w)
+				}
+			}
+			if len(wants) > 0 {
+				filtered := make([]ghapi.MilestoneIssue, 0, len(msIssues))
+			issueLoop:
+				for _, mi := range msIssues {
+					labelSet := make(map[string]struct{}, len(mi.Labels))
+					for _, l := range mi.Labels {
+						ln := strings.ToLower(strings.TrimSpace(l.Name))
+						if ln != "" {
+							labelSet[ln] = struct{}{}
+						}
+					}
+					for _, want := range wants {
+						if _, ok := labelSet[want]; !ok {
+							continue issueLoop
+						}
+					}
+					filtered = append(filtered, mi)
+				}
+				msIssues = filtered
+			}
+		}
+
+		// Extract numbers for project discovery (post filtering)
+		issueNums := make([]int, 0, len(msIssues))
+		for _, it := range msIssues {
+			issueNums = append(issueNums, it.Number)
+		}
+
+		// Determine all projects across these issues, dynamically
+		projects, _ := ghapi.GetProjectsForIssues(issueNums)
+		// Apply ignore-project filtering if provided
+		if strings.TrimSpace(milestoneIgnoreProject) != "" {
+			// build tokens (case-insensitive substring match)
+			parts := strings.Split(milestoneIgnoreProject, ",")
+			toks := make([]string, 0, len(parts))
+			for _, p := range parts {
+				t := strings.ToLower(strings.TrimSpace(p))
+				if t != "" {
+					toks = append(toks, t)
+				}
+			}
+			if len(toks) > 0 {
+				filtered := make([]ghapi.ProjectInfo, 0, len(projects))
+				for _, p := range projects {
+					title := p.Title
+					if title == "" {
+						// Without a title we can't match by name; keep it
+						filtered = append(filtered, p)
+						continue
+					}
+					name := strings.ToLower(stripEmojis(title))
+					exclude := false
+					for _, tok := range toks {
+						if tok != "" && strings.Contains(name, tok) {
+							exclude = true
+							break
+						}
+					}
+					if !exclude {
+						filtered = append(filtered, p)
+					}
+				}
+				projects = filtered
+			}
+		}
+		headers := make([]string, 0, len(projects)+2)
+		headers = append(headers, "Number")
+		for _, p := range projects {
+			if p.Title != "" {
+				title := p.Title
+				if milestoneStripEmojis {
+					title = stripEmojis(title)
+				}
+				headers = append(headers, title)
+			} else {
+				headers = append(headers, fmt.Sprintf("%d", p.ID))
+			}
+		}
+		// Final column header for issue title
+		headers = append(headers, "Title")
+
+		format := strings.ToLower(strings.TrimSpace(milestoneFormat))
+		if format == "" {
+			format = "tsv"
+		}
+
+		switch format {
+		case "tsv":
+			// Print header as TSV
+			// Heading line first
+			fmt.Printf("Milestone\treport\t%s\n", milestoneName)
+			fmt.Println(strings.Join(headers, "\t"))
+		case "md", "markdown":
+			// Heading line first
+			fmt.Printf("|Milestone report %s|\n", milestoneName)
+			// Markdown header
+			fmt.Printf("| %s |\n", strings.Join(headers, " | "))
+			// Separator row
+			seps := make([]string, len(headers))
+			for i := range seps {
+				seps[i] = "---"
+			}
+			fmt.Printf("| %s |\n", strings.Join(seps, " | "))
+		default:
+			return fmt.Errorf("unsupported --format %q (use: tsv or md)", milestoneFormat)
+		}
+
+		// Aggregator: projectID -> status -> count (only when Present)
+		agg := make(map[int]map[string]int, len(projects))
+
+		// For each issue, gather statuses per project
+		for _, mi := range msIssues {
+			num := mi.Number
+			// Build the list of project IDs in header order
+			pids := make([]int, 0, len(projects))
+			for _, p := range projects {
+				pids = append(pids, p.ID)
+			}
+			statuses, _ := ghapi.GetIssueProjectStatuses(num, pids)
+			row := []string{fmt.Sprintf("%d", num)}
+			for _, pid := range pids {
+				ps, ok := statuses[pid]
+				if !ok || !ps.Present {
+					row = append(row, "-")
+					continue
+				}
+				if strings.TrimSpace(ps.Status) == "" {
+					cell := "No Status"
+					if milestoneStripEmojis {
+						cell = stripEmojis(cell)
+					}
+					row = append(row, cell)
+					if agg[pid] == nil {
+						agg[pid] = make(map[string]int)
+					}
+					agg[pid]["No Status"]++
+				} else {
+					cell := ps.Status
+					if milestoneStripEmojis {
+						cell = stripEmojis(cell)
+					}
+					row = append(row, cell)
+					if agg[pid] == nil {
+						agg[pid] = make(map[string]int)
+					}
+					agg[pid][ps.Status]++
+				}
+			}
+			// Append truncated title column
+			title := mi.Title
+			if milestoneStripEmojis {
+				title = stripEmojis(title)
+			}
+			row = append(row, truncateTitle(title, 25))
+			if format == "tsv" {
+				fmt.Println(strings.Join(row, "\t"))
+			} else {
+				fmt.Printf("| %s |\n", strings.Join(row, " | "))
+			}
+		}
+
+		// Build and print summary rows: Project, Status, Count
+		type sumRow struct {
+			Project   string
+			ProjectID int
+			Status    string
+			Count     int
+		}
+		rows := make([]sumRow, 0)
+		// helper: title by pid
+		getProjTitle := func(pid int) string {
+			for _, p := range projects {
+				if p.ID == pid {
+					return p.Title
+				}
+			}
+			return fmt.Sprintf("%d", pid)
+		}
+		for pid, m := range agg {
+			title := getProjTitle(pid)
+			for status, c := range m {
+				rows = append(rows, sumRow{Project: title, ProjectID: pid, Status: status, Count: c})
+			}
+		}
+		if len(rows) > 0 {
+			// sorting: default by count asc; if --summary-sort name, sort by project name (emoji-stripped), then status
+			key := strings.ToLower(strings.TrimSpace(milestoneSummarySort))
+			if key == "" {
+				key = "count"
+			}
+			sort.Slice(rows, func(i, j int) bool {
+				if key == "name" {
+					pi := plainForSort(rows[i].Project)
+					pj := plainForSort(rows[j].Project)
+					if pi != pj {
+						return pi < pj
+					}
+					si := plainForSort(rows[i].Status)
+					sj := plainForSort(rows[j].Status)
+					if si != sj {
+						return si < sj
+					}
+					if rows[i].Count != rows[j].Count {
+						return rows[i].Count < rows[j].Count
+					}
+					return rows[i].ProjectID < rows[j].ProjectID
+				}
+				if rows[i].Count != rows[j].Count {
+					return rows[i].Count < rows[j].Count
+				}
+				pi := plainForSort(rows[i].Project)
+				pj := plainForSort(rows[j].Project)
+				if pi != pj {
+					return pi < pj
+				}
+				si := plainForSort(rows[i].Status)
+				sj := plainForSort(rows[j].Status)
+				if si != sj {
+					return si < sj
+				}
+				return rows[i].ProjectID < rows[j].ProjectID
+			})
+
+			if format == "tsv" {
+				fmt.Println()
+				fmt.Println("Summary")
+				fmt.Println(strings.Join([]string{"Project", "Status", "Count"}, "\t"))
+				for _, r := range rows {
+					proj := r.Project
+					stat := r.Status
+					if milestoneStripEmojis {
+						proj = stripEmojis(proj)
+						stat = stripEmojis(stat)
+					}
+					fmt.Println(strings.Join([]string{proj, stat, fmt.Sprintf("%d", r.Count)}, "\t"))
+				}
+			} else {
+				fmt.Println()
+				fmt.Println("Summary")
+				fmt.Printf("| %s |\n", strings.Join([]string{"Project", "Status", "Count"}, " | "))
+				fmt.Printf("| %s |\n", strings.Join([]string{"---", "---", "---"}, " | "))
+				for _, r := range rows {
+					proj := r.Project
+					stat := r.Status
+					if milestoneStripEmojis {
+						proj = stripEmojis(proj)
+						stat = stripEmojis(stat)
+					}
+					fmt.Printf("| %s | %s | %d |\n", proj, stat, r.Count)
+				}
+			}
+		}
+		return nil
+	},
+}
+
+func init() {
+	milestoneCmd.AddCommand(milestoneReportCmd)
+	milestoneReportCmd.Flags().StringVar(&milestoneFormat, "format", "tsv", "Output format: tsv (default) or md")
+	milestoneReportCmd.Flags().BoolVar(&milestoneStripEmojis, "strip-emojis", false, "Strip emojis from project titles and statuses")
+	milestoneReportCmd.Flags().StringVar(&milestoneSummarySort, "summary-sort", "count", "Summary sort: count (default) or name")
+	milestoneReportCmd.Flags().BoolVar(&milestoneIncludeClosed, "include-closed", false, "Include closed milestones when listing available milestones")
+	milestoneReportCmd.Flags().StringVar(&milestoneIgnoreProject, "ignore-project", "", "Comma-separated substrings to exclude matching project titles (case-insensitive). Example: 'qa,cust' excludes ':help-qa', ':help-customers', and 'Customer requests (open)'.")
+	milestoneReportCmd.Flags().StringVar(&milestoneFilterLabels, "filter-labels", "", "Comma-separated list of labels; only issues containing ALL of these labels are included (case-insensitive). Example: 'story,customer-numa'.")
+}
+
+// stripEmojis removes common emoji and pictographic characters from a string,
+// including variation selectors and zero-width joiners, leaving readable text.
+func stripEmojis(s string) string {
+	var b strings.Builder
+	for _, r := range s {
+		// Skip variation selector and zero-width joiners/spaces
+		if r == 0xFE0F || r == 0x200D || r == 0x200C || r == 0x200B {
+			continue
+		}
+		// Common emoji blocks and symbols/pictographs
+		if (r >= 0x1F300 && r <= 0x1FAFF) || // Misc symbols & pictographs to Supplemental symbols
+			(r >= 0x2600 && r <= 0x27BF) { // Misc symbols + Dingbats
+			continue
+		}
+		b.WriteRune(r)
+	}
+	return strings.TrimSpace(b.String())
+}
+
+// plainForSort returns a simplified string without emojis, lowercased, for consistent sorting
+func plainForSort(s string) string {
+	return strings.ToLower(stripEmojis(s))
+}
+
+// truncateTitle truncates a string to maxRunes characters (by rune count) and appends
+// "..." if the original was longer. The ellipsis is not counted toward maxRunes.
+func truncateTitle(s string, maxRunes int) string {
+	if maxRunes <= 0 {
+		return ""
+	}
+	count := 0
+	for idx := range s {
+		if count == maxRunes {
+			// idx is byte index at rune boundary for the first runes
+			return s[:idx] + "..."
+		}
+		count++
+	}
+	return s
+}
diff --git a/tools/github-manage/cmd/gm/project.go b/tools/github-manage/cmd/gm/project.go
index 03d411f511..05fe7533a4 100644
--- a/tools/github-manage/cmd/gm/project.go
+++ b/tools/github-manage/cmd/gm/project.go
@@ -34,6 +34,7 @@ func init() {
 	projectCmd.Flags().IntP("limit", "l", 100, "Maximum number of items to fetch")
 	estimatedCmd.Flags().IntP("limit", "l", 500, "Maximum number of items to fetch from drafting project")
 	sprintCmd.Flags().IntP("limit", "l", 100, "Maximum number of items to fetch")
+	sprintCmd.Flags().BoolP("previous", "p", false, "Show previous sprint instead of current")
 }
 
 var estimatedCmd = &cobra.Command{
@@ -62,7 +63,7 @@ var estimatedCmd = &cobra.Command{
 // current iteration (using the already implemented @current logic when setting sprint).
 var sprintCmd = &cobra.Command{
 	Use:   "sprint [project-id-or-alias]",
-	Short: "Get GitHub issues in the current sprint for a project",
+	Short: "Get GitHub issues in the current sprint for a project (use -p for previous sprint)",
 	Args:  cobra.ExactArgs(1),
 	Run: func(cmd *cobra.Command, args []string) {
 		projectID, err := ghapi.ResolveProjectID(args[0])
@@ -77,6 +78,13 @@ var sprintCmd = &cobra.Command{
 			return
 		}
 
+		prev, _ := cmd.Flags().GetBool("previous")
+		if prev {
+			// Pass a mode hint via the search parameter
+			tui.RunTUI(tui.SprintCommand, projectID, limit, "previous")
+			return
+		}
+
 		tui.RunTUI(tui.SprintCommand, projectID, limit, "")
 	},
 }
diff --git a/tools/github-manage/cmd/gm/roadmap.go b/tools/github-manage/cmd/gm/roadmap.go
new file mode 100644
index 0000000000..5f50a1cde2
--- /dev/null
+++ b/tools/github-manage/cmd/gm/roadmap.go
@@ -0,0 +1,160 @@
+package main
+
+import (
+	"fmt"
+	"sort"
+	"strings"
+
+	"fleetdm/gm/pkg/ghapi"
+
+	"github.com/spf13/cobra"
+)
+
+var roadmapCmd = &cobra.Command{
+	Use:   "roadmap",
+	Short: "Roadmap utilities",
+}
+
+var roadmapSyncEstimatesCmd = &cobra.Command{
+	Use:   "sync-estimates",
+	Short: "Sync estimates for issues on the Roadmap project from drafting/sprint projects or sub-issues",
+	Run: func(cmd *cobra.Command, args []string) {
+		roadmapProjectID := 87 // fleet Roadmap project
+
+		issueNum, _ := cmd.Flags().GetInt("issue")
+		overwrite, _ := cmd.Flags().GetBool("overwrite")
+		sprintTitle, _ := cmd.Flags().GetString("sprint")
+
+		// Define candidate source projects for estimates
+		sources := ghapi.DefaultEstimateSourceProjects()
+
+		var targets []int
+		if issueNum > 0 {
+			fmt.Printf("Checking Roadmap membership for #%d...\n", issueNum)
+			targets = []int{issueNum}
+			// Ensure the specified issue is on Roadmap
+			if !ghapi.IsIssueInProject(issueNum, roadmapProjectID) {
+				fmt.Printf("Error: issue #%d is not currently on the Roadmap project (%d)\n", issueNum, roadmapProjectID)
+				return
+			}
+			fmt.Printf("Gathering estimates for #%d...\n", issueNum)
+			// Optional sprint filter for single issue
+			if sprintTitle != "" {
+				fmt.Printf("Filtering by sprint '%s'...\n", sprintTitle)
+				checkProjects := append(append([]int{}, sources...), roadmapProjectID)
+				sprintSet, _ := ghapi.GetIssueNumbersForSprintAcrossProjects(checkProjects, sprintTitle, 2000)
+				if _, ok := sprintSet[issueNum]; !ok {
+					fmt.Printf("Issue #%d is not in sprint '%s' across known projects; skipping.\n", issueNum, sprintTitle)
+					return
+				}
+				fmt.Printf("Issue #%d matched sprint '%s'.\n", issueNum, sprintTitle)
+			}
+		} else {
+			fmt.Println("Finding Roadmap issues...")
+			// Fetch all roadmap issues
+			items, _, err := ghapi.GetProjectItemsWithTotal(roadmapProjectID, 1000)
+			if err != nil {
+				fmt.Printf("Failed to fetch roadmap items: %v\n", err)
+				return
+			}
+			for _, it := range items {
+				if it.Content.Number > 0 {
+					targets = append(targets, it.Content.Number)
+				}
+			}
+			fmt.Printf("Found %d Roadmap issues.\n", len(targets))
+
+			// Apply sprint filter if provided
+			if sprintTitle != "" {
+				fmt.Printf("Filtering by sprint '%s'...\n", sprintTitle)
+				// Build sprint set from source projects only to avoid re-querying Roadmap (we already have its items)
+				sprintSet, _ := ghapi.GetIssueNumbersForSprintAcrossProjects(sources, sprintTitle, 2000)
+				filtered := make([]int, 0, len(targets))
+				for _, n := range targets {
+					// include if in sources' sprint set or roadmap item shows matching sprint
+					_, inSet := sprintSet[n]
+					if inSet {
+						filtered = append(filtered, n)
+						continue
+					}
+					// check roadmap item sprint title from prefetched items
+					for _, it := range items {
+						if it.Content.Number == n && it.Sprint != nil && strings.EqualFold(strings.TrimSpace(it.Sprint.Title), strings.TrimSpace(sprintTitle)) {
+							filtered = append(filtered, n)
+							break
+						}
+					}
+				}
+				targets = filtered
+				fmt.Printf("%d issues match sprint '%s'.\n", len(targets), sprintTitle)
+			}
+		}
+
+		// Make iteration stable for output
+		sort.Ints(targets)
+
+		var (
+			updated int
+			skipped int
+			errors  int
+		)
+
+		for _, n := range targets {
+			fmt.Printf("\nGathering estimate for #%d...\n", n)
+			// Skip if roadmap already has estimate and --all-issues not provided
+			if !overwrite {
+				if val, ok, _ := ghapi.GetEstimateFromProject(n, roadmapProjectID); ok && val > 0 {
+					skipped++
+					fmt.Printf("Skipping #%d: roadmap estimate already set to %d\n", n, val)
+					continue
+				}
+			}
+
+			// Primary: direct estimate from known projects
+			est, src, _ := ghapi.GetEstimateForIssueAcrossProjects(n, sources)
+			if est > 0 && src > 0 {
+				fmt.Printf("Found estimate %d in project %d.\n", est, src)
+			}
+			// Secondary: sum of sub-issue estimates
+			if est == 0 {
+				related, _ := ghapi.GetRelatedIssueNumbers(n)
+				if len(related) > 0 {
+					fmt.Printf("Found %d issues tied to #%d...\n", len(related), n)
+				} else {
+					fmt.Printf("No direct estimate found; checking sub-issues for #%d...\n", n)
+				}
+				sum, _ := ghapi.SumEstimatesFromSubIssues(n, sources)
+				est = sum
+				src = 0 // aggregated
+				if est > 0 {
+					fmt.Printf("Using aggregated sub-issue estimate: %d.\n", est)
+				}
+			}
+			if est == 0 {
+				fmt.Printf("No estimate found for #%d; leaving roadmap unchanged\n", n)
+				continue
+			}
+
+			if err := ghapi.SetEstimateInProject(n, roadmapProjectID, est); err != nil {
+				errors++
+				fmt.Printf("Failed to set roadmap estimate for #%d: %v\n", n, err)
+				continue
+			}
+			updated++
+			if src == 0 {
+				fmt.Printf("Updated #%d: roadmap estimate set to %d (sum of sub-issues)\n", n, est)
+			} else {
+				fmt.Printf("Updated #%d: roadmap estimate set to %d (from project %d)\n", n, est, src)
+			}
+		}
+
+		fmt.Printf("\nSummary: %d updated, %d skipped, %d errors\n", updated, skipped, errors)
+	},
+}
+
+func init() {
+	roadmapCmd.AddCommand(roadmapSyncEstimatesCmd)
+	roadmapSyncEstimatesCmd.Flags().IntP("issue", "i", 0, "Only sync for the given issue number; must be on the Roadmap project")
+	roadmapSyncEstimatesCmd.Flags().BoolP("overwrite", "o", false, "Overwrite existing Roadmap estimates (by default, issues with estimates are skipped)")
+	roadmapSyncEstimatesCmd.Flags().StringP("sprint", "s", "", "Only process issues in this sprint (iteration title), e.g., 4.77.0")
+}
diff --git a/tools/github-manage/pkg/ghapi/estimates.go b/tools/github-manage/pkg/ghapi/estimates.go
new file mode 100644
index 0000000000..618312434a
--- /dev/null
+++ b/tools/github-manage/pkg/ghapi/estimates.go
@@ -0,0 +1,285 @@
+package ghapi
+
+import (
+	"encoding/json"
+	"fmt"
+	"strconv"
+	"strings"
+	"sync"
+)
+
+// DefaultEstimateSourceProjects returns the default set of projects to scan for estimates
+// when syncing to Roadmap: drafting and product group projects.
+func DefaultEstimateSourceProjects() []int {
+	// unique list; ignore roadmap itself (87) as a source
+	return []int{Aliases["draft"], Aliases["mdm"], Aliases["g-software"], Aliases["g-orchestration"], Aliases["g-security-compliance"]}
+}
+
+// GetEstimateFromProject returns the numeric estimate for an issue from a specific project.
+// Second return indicates whether a non-zero estimate was found.
+func GetEstimateFromProject(issueNumber int, projectID int) (int, bool, error) {
+	itemID, err := GetProjectItemID(issueNumber, projectID)
+	if err != nil {
+		return 0, false, err
+	}
+	val, err := getProjectItemFieldValue(itemID, projectID, "Estimate")
+	if err != nil {
+		return 0, false, err
+	}
+	if val == "" || val == "0" {
+		return 0, false, nil
+	}
+	i, convErr := strconv.Atoi(val)
+	if convErr != nil {
+		return 0, false, fmt.Errorf("invalid estimate value '%s' for issue #%d in project %d", val, issueNumber, projectID)
+	}
+	return i, true, nil
+}
+
+// GetEstimateForIssueAcrossProjects scans the provided projects in order and returns
+// the first non-zero estimate found for the issue, along with the project ID that provided it.
+func GetEstimateForIssueAcrossProjects(issueNumber int, projects []int) (int, int, error) {
+	// Efficient path: single per-issue GraphQL to fetch all project item estimates.
+	m, err := getIssueEstimatesAcrossProjects(issueNumber)
+	if err == nil {
+		for _, pid := range projects {
+			if v, ok := m[pid]; ok && v > 0 {
+				return v, pid, nil
+			}
+		}
+		for pid, v := range m {
+			if v > 0 {
+				return v, pid, nil
+			}
+		}
+		return 0, 0, nil
+	}
+	// Fallback path (older approach) if GraphQL fails: check projects one by one
+	for _, pid := range projects {
+		itemID, e := GetProjectItemID(issueNumber, pid)
+		if e != nil {
+			continue
+		}
+		val, e := getProjectItemFieldValue(itemID, pid, "Estimate")
+		if e != nil || val == "" || val == "0" {
+			continue
+		}
+		if i, convErr := strconv.Atoi(val); convErr == nil && i > 0 {
+			return i, pid, nil
+		}
+	}
+	return 0, 0, nil
+}
+
+// SumEstimatesFromSubIssues sums the estimates of direct sub-issues (one level)
+// using the first-found estimate across the provided projects for each child.
+func SumEstimatesFromSubIssues(issueNumber int, projects []int) (int, error) {
+	children, err := GetRelatedIssueNumbers(issueNumber)
+	if err != nil {
+		return 0, err
+	}
+	if len(children) == 0 {
+		return 0, nil
+	}
+	sum := 0
+	for _, child := range children {
+		if est, _, _ := GetEstimateFromAnyProject(child, projects); est > 0 {
+			sum += est
+		}
+	}
+	return sum, nil
+}
+
+// IsIssueInProject checks whether an issue is a member of the given project.
+func IsIssueInProject(issueNumber int, projectID int) bool {
+	_, err := GetProjectItemID(issueNumber, projectID)
+	if err != nil {
+		return false
+	}
+	return true
+}
+
+// SetEstimateInProject sets the Estimate field for the given issue in the specified project.
+func SetEstimateInProject(issueNumber int, projectID int, estimate int) error {
+	// Defensive: never set zero/negative estimates; treat as "leave blank"
+	if estimate <= 0 {
+		return nil
+	}
+	itemID, err := GetProjectItemID(issueNumber, projectID)
+	if err != nil {
+		return fmt.Errorf("failed to get project item for issue #%d in project %d: %v", issueNumber, projectID, err)
+	}
+	return SetProjectItemFieldValue(itemID, projectID, "Estimate", strconv.Itoa(estimate))
+}
+
+// IssueInSprint checks whether the given issue has the specified sprint title in any of the provided projects.
+// Returns true along with the project ID where the match was found.
+func IssueInSprint(issueNumber int, sprintTitle string, projects []int) (bool, int) {
+	st := strings.TrimSpace(sprintTitle)
+	if st == "" {
+		return false, 0
+	}
+	for _, pid := range projects {
+		itemID, err := GetProjectItemID(issueNumber, pid)
+		if err != nil {
+			continue
+		}
+		title, err := getProjectItemFieldValue(itemID, pid, "Sprint")
+		if err != nil || strings.TrimSpace(title) == "" {
+			continue
+		}
+		if strings.EqualFold(strings.TrimSpace(title), st) {
+			return true, pid
+		}
+	}
+	return false, 0
+}
+
+// GetIssueNumbersForSprint returns all issue numbers in the given project whose Sprint title matches.
+func GetIssueNumbersForSprint(projectID int, sprintTitle string, limit int) ([]int, error) {
+	st := strings.TrimSpace(sprintTitle)
+	if st == "" {
+		return []int{}, nil
+	}
+	items, _, err := GetProjectItemsWithTotal(projectID, limit)
+	if err != nil {
+		return nil, err
+	}
+	var nums []int
+	for _, it := range items {
+		if it.Content.Number == 0 || it.Sprint == nil {
+			continue
+		}
+		if strings.EqualFold(strings.TrimSpace(it.Sprint.Title), st) {
+			nums = append(nums, it.Content.Number)
+		}
+	}
+	return nums, nil
+}
+
+// GetIssueNumbersForSprintAcrossProjects builds a union set of issue numbers
+// that are in the specified sprint across multiple projects.
+func GetIssueNumbersForSprintAcrossProjects(projectIDs []int, sprintTitle string, limit int) (map[int]struct{}, error) {
+	out := make(map[int]struct{})
+	for _, pid := range projectIDs {
+		nums, err := GetIssueNumbersForSprint(pid, sprintTitle, limit)
+		if err != nil {
+			// Skip problematic project but continue others
+			continue
+		}
+		for _, n := range nums {
+			out[n] = struct{}{}
+		}
+	}
+	return out, nil
+}
+
+// --- Efficient per-issue estimate discovery via GraphQL ---
+
+var (
+	issueEstimateCache   = make(map[int]map[int]int) // issue -> (projectNumber -> estimate)
+	issueEstimateCacheMu sync.RWMutex
+)
+
+// getIssueEstimatesAcrossProjects fetches all project items for the issue and returns
+// a map of project number -> Estimate value (if present and >0).
+func getIssueEstimatesAcrossProjects(issueNumber int) (map[int]int, error) {
+	// Cache lookup
+	issueEstimateCacheMu.RLock()
+	if m, ok := issueEstimateCache[issueNumber]; ok {
+		issueEstimateCacheMu.RUnlock()
+		return m, nil
+	}
+	issueEstimateCacheMu.RUnlock()
+
+	owner, repo, err := getRepoOwnerAndName()
+	if err != nil {
+		return nil, err
+	}
+	query := `query($owner:String!,$repo:String!,$number:Int!){
+		repository(owner:$owner,name:$repo){
+			issue(number:$number){
+				projectItems(first:100){
+					nodes{
+						project{ number }
+						fieldValues(first:20){
+							nodes{
+								__typename
+								... on ProjectV2ItemFieldNumberValue{
+									number
+									field{ ... on ProjectV2FieldCommon{ name } }
+								}
+							}
+						}
+					}
+				}
+			}
+		}
+	}`
+	cmd := fmt.Sprintf("gh api graphql -f query='%s' -f owner='%s' -f repo='%s' -F number=%d", query, owner, repo, issueNumber)
+	out, err := RunCommandAndReturnOutput(cmd)
+	if err != nil {
+		return nil, err
+	}
+	var resp struct {
+		Data struct {
+			Repository struct {
+				Issue struct {
+					ProjectItems struct {
+						Nodes []struct {
+							Project struct{ Number int `json:"number"` } `json:"project"`
+							FieldValues struct{
+								Nodes []struct{
+									Typename string  `json:"__typename"`
+									Number   *float64 `json:"number,omitempty"`
+									Field    struct{
+										Name string `json:"name"`
+									} `json:"field"`
+								} `json:"nodes"`
+							} `json:"fieldValues"`
+						} `json:"nodes"`
+					} `json:"projectItems"`
+				} `json:"issue"`
+			} `json:"repository"`
+		} `json:"data"`
+	}
+	if err := json.Unmarshal(out, &resp); err != nil {
+		return nil, err
+	}
+	result := make(map[int]int)
+	for _, it := range resp.Data.Repository.Issue.ProjectItems.Nodes {
+		pid := it.Project.Number
+		for _, fv := range it.FieldValues.Nodes {
+			if strings.EqualFold(fv.Field.Name, "Estimate") && fv.Number != nil {
+				v := int(*fv.Number)
+				if v > 0 {
+					result[pid] = v
+				}
+			}
+		}
+	}
+	issueEstimateCacheMu.Lock()
+	issueEstimateCache[issueNumber] = result
+	issueEstimateCacheMu.Unlock()
+	return result, nil
+}
+
+// GetEstimateFromAnyProject returns the first positive estimate found for the issue,
+// preferring the provided project order when specified.
+func GetEstimateFromAnyProject(issueNumber int, preferredProjects []int) (int, int, error) {
+	m, err := getIssueEstimatesAcrossProjects(issueNumber)
+	if err != nil {
+		return 0, 0, err
+	}
+	for _, pid := range preferredProjects {
+		if v, ok := m[pid]; ok && v > 0 {
+			return v, pid, nil
+		}
+	}
+	for pid, v := range m {
+		if v > 0 {
+			return v, pid, nil
+		}
+	}
+	return 0, 0, nil
+}
diff --git a/tools/github-manage/pkg/ghapi/milestone.go b/tools/github-manage/pkg/ghapi/milestone.go
new file mode 100644
index 0000000000..b2717423d3
--- /dev/null
+++ b/tools/github-manage/pkg/ghapi/milestone.go
@@ -0,0 +1,355 @@
+package ghapi
+
+import (
+	"bytes"
+	"encoding/json"
+	"fmt"
+	"os/exec"
+	"sort"
+	"strings"
+	"time"
+
+	"fleetdm/gm/pkg/logger"
+)
+
+// GetIssuesByMilestone returns issue numbers for a given milestone name. Limit controls max items.
+func GetIssuesByMilestone(name string, limit int) ([]int, error) {
+	if limit <= 0 {
+		limit = 1000
+	}
+	// Use gh to list issues for the current repo by milestone
+	// Include closed/open (state all) to reflect full milestone scope
+	cmd := fmt.Sprintf("gh issue list --state all --milestone %q --limit %d --json number", name, limit)
+	out, err := RunCommandAndReturnOutput(cmd)
+	if err != nil {
+		return nil, err
+	}
+	var arr []struct {
+		Number int `json:"number"`
+	}
+	if err := json.Unmarshal(out, &arr); err != nil {
+		return nil, err
+	}
+	nums := make([]int, 0, len(arr))
+	for _, it := range arr {
+		nums = append(nums, it.Number)
+	}
+	return nums, nil
+}
+
+// GetIssuesByMilestoneWithTitles returns issue numbers and titles for a milestone.
+func GetIssuesByMilestoneWithTitles(name string, limit int) ([]MilestoneIssue, error) {
+	if limit <= 0 {
+		limit = 1000
+	}
+	cmd := fmt.Sprintf("gh issue list --state all --milestone %q --limit %d --json number,title,labels", name, limit)
+	out, err := RunCommandAndReturnOutput(cmd)
+	if err != nil {
+		return nil, err
+	}
+	var arr []MilestoneIssue
+	if err := json.Unmarshal(out, &arr); err != nil {
+		return nil, err
+	}
+	return arr, nil
+}
+
+// ProjectInfo represents a GitHub Project (v2) basic descriptor used in reports.
+type ProjectInfo struct {
+	ID    int    // project number (e.g., 58)
+	Title string // project title (e.g., g-mdm)
+}
+
+// MilestoneIssue represents a simple issue record for a milestone.
+type MilestoneIssue struct {
+	Number int    `json:"number"`
+	Title  string `json:"title"`
+	Labels []struct {
+		Name string `json:"name"`
+	} `json:"labels"`
+}
+
+// GetIssueProjects returns projects (id->title) that a specific issue belongs to.
+func GetIssueProjects(issueNumber int) (map[int]string, error) {
+	owner, repo, err := getRepoOwnerAndName()
+	if err != nil {
+		return nil, err
+	}
+	query := `query($owner:String!,$repo:String!,$number:Int!){
+        repository(owner:$owner,name:$repo){
+            issue(number:$number){
+                projectItems(first:50){
+                    nodes{
+                        project{ number title }
+                    }
+                }
+            }
+        }
+    }`
+	cmd := fmt.Sprintf("gh api graphql -f query='%s' -f owner='%s' -f repo='%s' -F number=%d", query, owner, repo, issueNumber)
+	out, err := RunCommandAndReturnOutput(cmd)
+	if err != nil {
+		return nil, err
+	}
+	var resp struct {
+		Data struct {
+			Repository struct {
+				Issue struct {
+					ProjectItems struct {
+						Nodes []struct {
+							Project struct {
+								Number int    `json:"number"`
+								Title  string `json:"title"`
+							} `json:"project"`
+						} `json:"nodes"`
+					} `json:"projectItems"`
+				} `json:"issue"`
+			} `json:"repository"`
+		} `json:"data"`
+	}
+	if err := json.Unmarshal(out, &resp); err != nil {
+		return nil, err
+	}
+	m := make(map[int]string)
+	for _, n := range resp.Data.Repository.Issue.ProjectItems.Nodes {
+		if n.Project.Number != 0 {
+			m[n.Project.Number] = n.Project.Title
+		}
+	}
+	return m, nil
+}
+
+// GetProjectsForIssues gathers the union of projects across the provided issues.
+func GetProjectsForIssues(issueNumbers []int) ([]ProjectInfo, error) {
+	seen := make(map[int]string)
+	for _, num := range issueNumbers {
+		prjs, err := GetIssueProjects(num)
+		if err != nil {
+			// tolerate errors per-issue, continue accumulating from others
+			continue
+		}
+		for id, title := range prjs {
+			if _, ok := seen[id]; !ok {
+				seen[id] = title
+			}
+		}
+	}
+	list := make([]ProjectInfo, 0, len(seen))
+	for id, title := range seen {
+		list = append(list, ProjectInfo{ID: id, Title: title})
+	}
+	// stable order: by title then id
+	sort.Slice(list, func(i, j int) bool {
+		if list[i].Title == list[j].Title {
+			return list[i].ID < list[j].ID
+		}
+		return list[i].Title < list[j].Title
+	})
+	return list, nil
+}
+
+// GetIssueProjectStatuses returns a map of projectID -> Status value for an issue across given projects.
+// If the issue is not present in a project or the Status is unset, the value will be an empty string.
+type ProjectStatus struct {
+	Present bool   // true if the issue is in this project
+	Status  string // "" when unset
+}
+
+func GetIssueProjectStatuses(issueNumber int, projects []int) (map[int]ProjectStatus, error) {
+	// Single GraphQL query to fetch all project items and their Status field for this issue
+	owner, repo, err := getRepoOwnerAndName()
+	if err != nil {
+		// If repo cannot be determined, return absent for all
+		res := make(map[int]ProjectStatus, len(projects))
+		for _, pid := range projects {
+			res[pid] = ProjectStatus{Present: false, Status: ""}
+		}
+		return res, nil
+	}
+
+	query := `query($owner:String!,$repo:String!,$number:Int!){
+		repository(owner:$owner,name:$repo){
+			issue(number:$number){
+				projectItems(first:100){
+					nodes{
+						project{ number title }
+						fieldValues(first:50){
+							nodes{
+								__typename
+								... on ProjectV2ItemFieldSingleSelectValue{
+									field{ ... on ProjectV2FieldCommon{ name } }
+									name
+								}
+							}
+						}
+					}
+				}
+			}
+		}
+	}`
+	cmd := fmt.Sprintf("gh api graphql -f query='%s' -f owner='%s' -f repo='%s' -F number=%d", query, owner, repo, issueNumber)
+	out, err := runCommandWithRetry(cmd, 5, 2*time.Second)
+	if err != nil {
+		// On error, default to absent for all requested projects
+		res := make(map[int]ProjectStatus, len(projects))
+		for _, pid := range projects {
+			res[pid] = ProjectStatus{Present: false, Status: ""}
+		}
+		return res, nil
+	}
+	var resp struct {
+		Data struct {
+			Repository struct {
+				Issue struct {
+					ProjectItems struct {
+						Nodes []struct {
+							Project struct {
+								Number int    `json:"number"`
+								Title  string `json:"title"`
+							} `json:"project"`
+							FieldValues struct {
+								Nodes []struct {
+									Typename string `json:"__typename"`
+									Field    struct {
+										Name string `json:"name"`
+									} `json:"field"`
+									Name string `json:"name"`
+								} `json:"nodes"`
+							} `json:"fieldValues"`
+						} `json:"nodes"`
+					} `json:"projectItems"`
+				} `json:"issue"`
+			} `json:"repository"`
+		} `json:"data"`
+	}
+	if err := json.Unmarshal(out, &resp); err != nil {
+		res := make(map[int]ProjectStatus, len(projects))
+		for _, pid := range projects {
+			res[pid] = ProjectStatus{Present: false, Status: ""}
+		}
+		return res, nil
+	}
+
+	// Build a map of project number -> status value
+	found := make(map[int]ProjectStatus)
+	for _, node := range resp.Data.Repository.Issue.ProjectItems.Nodes {
+		pid := node.Project.Number
+		statusVal := ""
+		for _, fv := range node.FieldValues.Nodes {
+			if strings.EqualFold(fv.Field.Name, "Status") && fv.Typename == "ProjectV2ItemFieldSingleSelectValue" {
+				statusVal = fv.Name
+				break
+			}
+		}
+		found[pid] = ProjectStatus{Present: true, Status: statusVal}
+	}
+
+	// Compose response for requested projects, marking absences with Present=false
+	res := make(map[int]ProjectStatus, len(projects))
+	for _, pid := range projects {
+		if ps, ok := found[pid]; ok {
+			res[pid] = ps
+		} else {
+			res[pid] = ProjectStatus{Present: false, Status: ""}
+		}
+	}
+	return res, nil
+}
+
+// runCommandWithRetry executes a shell command capturing combined output and retries with
+// exponential backoff when a rate limit is detected in the output.
+func runCommandWithRetry(command string, attempts int, baseDelay time.Duration) ([]byte, error) {
+	if attempts < 1 {
+		attempts = 1
+	}
+	delay := baseDelay
+	for i := 1; i <= attempts; i++ {
+		logger.Debugf("Running COMMAND (attempt %d/%d): %s", i, attempts, command)
+		cmd := exec.Command("bash", "-c", command)
+		var out bytes.Buffer
+		cmd.Stdout = &out
+		cmd.Stderr = &out
+		err := cmd.Run()
+		if err == nil {
+			return out.Bytes(), nil
+		}
+		outStr := out.String()
+		logger.Errorf("Error running command (attempt %d): %s", i, outStr)
+		if i == attempts || !looksLikeRateLimit(outStr) {
+			return nil, err
+		}
+		logger.Infof("Rate limit detected; backing off for %s before retry", delay)
+		time.Sleep(delay)
+		// Exponential backoff with cap
+		if delay < 30*time.Second {
+			delay = delay * 2
+			if delay > 30*time.Second {
+				delay = 30 * time.Second
+			}
+		}
+	}
+	return nil, fmt.Errorf("command failed after %d attempts", attempts)
+}
+
+func looksLikeRateLimit(s string) bool {
+	ls := strings.ToLower(s)
+	if strings.Contains(ls, "rate limit") || strings.Contains(ls, "graphql_rate_limit") || strings.Contains(ls, "429") {
+		return true
+	}
+	return false
+}
+
+// RepoMilestone represents a repository milestone (from REST API).
+type RepoMilestone struct {
+	Number int    `json:"number"`
+	Title  string `json:"title"`
+	State  string `json:"state"`
+}
+
+// ListRepoMilestones returns milestones for the current repository.
+// When includeClosed is false, only open milestones are returned; otherwise all states are included.
+func ListRepoMilestones(includeClosed bool) ([]RepoMilestone, error) {
+	owner, repo, err := getRepoOwnerAndName()
+	if err != nil {
+		return nil, err
+	}
+	state := "open"
+	if includeClosed {
+		state = "all"
+	}
+	// Paginate to ensure we gather more than one page if present
+	all := make([]RepoMilestone, 0)
+	for page := 1; page <= 10; page++ { // hard cap to avoid accidental infinite loops
+		cmd := fmt.Sprintf("gh api repos/%s/%s/milestones?state=%s&per_page=100&page=%d", owner, repo, state, page)
+		out, err := RunCommandAndReturnOutput(cmd)
+		if err != nil {
+			return nil, err
+		}
+		var arr []RepoMilestone
+		if err := json.Unmarshal(out, &arr); err != nil {
+			return nil, err
+		}
+		if len(arr) == 0 {
+			break
+		}
+		all = append(all, arr...)
+		if len(arr) < 100 {
+			break
+		}
+	}
+	// Sort open first by title, then closed by title
+	sort.Slice(all, func(i, j int) bool {
+		si := strings.ToLower(all[i].State)
+		sj := strings.ToLower(all[j].State)
+		if si != sj {
+			if si == "open" {
+				return true
+			}
+			if sj == "open" {
+				return false
+			}
+		}
+		return strings.ToLower(all[i].Title) < strings.ToLower(all[j].Title)
+	})
+	return all, nil
+}
diff --git a/tools/github-manage/pkg/ghapi/projects.go b/tools/github-manage/pkg/ghapi/projects.go
index 7294d98110..47f853ffb8 100644
--- a/tools/github-manage/pkg/ghapi/projects.go
+++ b/tools/github-manage/pkg/ghapi/projects.go
@@ -7,26 +7,31 @@ import (
 	"fmt"
 	"strconv"
 	"strings"
+	"time"
 
 	"fleetdm/gm/pkg/logger"
 )
 
 var Aliases = map[string]int{
-	"mdm":             58,
-	"g-mdm":           58,
-	"draft":           67,
-	"drafting":        67,
-	"g-software":      70,
-	"soft":            70,
-	"g-orchestration": 71,
-	"orch":            71,
+	"mdm":                   58,
+	"g-mdm":                 58,
+	"draft":                 67,
+	"drafting":              67,
+	"g-software":            70,
+	"soft":                  70,
+	"g-orchestration":       71,
+	"orch":                  71,
+	"sec":                   97,
+	"g-security-compliance": 97,
+	"roadmap":               87,
 }
 
 // ProjectLabels maps project IDs to their corresponding label filters for the drafting project
 var ProjectLabels = map[int]string{
-	58: "#g-mdm",           // mdm project
-	70: "#g-software",      // g-software project
-	71: "#g-orchestration", // g-orchestration project
+	58: "#g-mdm",                 // mdm project
+	70: "#g-software",            // g-software project
+	71: "#g-orchestration",       // g-orchestration project
+	97: "#g-security-compliance", // g-security-compliance project
 }
 
 // ResolveProjectID resolves a project identifier (alias or numeric string) to a project ID.
@@ -68,7 +73,7 @@ func ParseJSONtoProjectItems(jsonData []byte, limit int) ([]ProjectItem, int, er
 
 // GetProjectItemsWithTotal retrieves project items and returns the server reported total count.
 func GetProjectItemsWithTotal(projectID, limit int) ([]ProjectItem, int, error) {
-	results, err := RunCommandAndReturnOutput(fmt.Sprintf("gh project item-list --owner fleetdm --format json --limit %d %d", limit, projectID))
+	results, err := runCommandWithRetry(fmt.Sprintf("gh project item-list --owner fleetdm --format json --limit %d %d", limit, projectID), 5, 2*time.Second)
 	if err != nil {
 		return nil, 0, err
 	}
@@ -122,6 +127,47 @@ func GetCurrentSprintItems(projectID, limit int) ([]ProjectItem, error) { // bac
 	return items, err
 }
 
+// GetPreviousSprintItemsWithTotal returns only the items in the previous sprint for a project.
+// It mirrors GetCurrentSprintItemsWithTotal but selects the iteration immediately before current
+// based on the iteration field configuration ordering.
+func GetPreviousSprintItemsWithTotal(projectID, limit int) ([]ProjectItem, int, error) {
+	items, total, err := GetProjectItemsWithTotal(projectID, limit)
+	if err != nil {
+		return nil, 0, err
+	}
+	projectNodeID, err := getProjectNodeID(projectID)
+	if err != nil {
+		return nil, total, fmt.Errorf("failed to get project node id: %v", err)
+	}
+	sprintField, err := LookupProjectFieldName(projectID, "sprint")
+	if err != nil {
+		return []ProjectItem{}, total, nil // no sprint field
+	}
+	// Get current iteration details (ID, start date, duration)
+	curID, curStart, curDuration, err := getCurrentIterationDetails(projectNodeID, sprintField.ID)
+	if err != nil || curID == "" || curStart == "" || curDuration <= 0 {
+		return []ProjectItem{}, total, fmt.Errorf("failed to get current iteration details: %v", err)
+	}
+	// Compute previous iteration start date as ISO date string
+	prevStart, err := computePrevStartDate(curStart, curDuration)
+	if err != nil {
+		return []ProjectItem{}, total, fmt.Errorf("failed to compute previous iteration start date: %v", err)
+	}
+	var filtered []ProjectItem
+	for _, it := range items {
+		if it.Sprint != nil && strings.TrimSpace(it.Sprint.StartDate) == prevStart {
+			filtered = append(filtered, it)
+		}
+	}
+	return filtered, total, nil
+}
+
+// Backward compatible helper
+func GetPreviousSprintItems(projectID, limit int) ([]ProjectItem, error) {
+	items, _, err := GetPreviousSprintItemsWithTotal(projectID, limit)
+	return items, err
+}
+
 // GetProjectFields retrieves all fields for a specific project.
 func GetProjectFields(projectID int) (map[string]ProjectField, error) {
 	// Run the command to get project fields
@@ -556,6 +602,12 @@ func getProjectItemFieldValue(itemID string, projectID int, fieldName string) (s
 							}
 							name
 						}
+						... on ProjectV2ItemFieldIterationValue {
+							field { ... on ProjectV2FieldCommon { id } }
+							title
+							startDate
+							duration
+						}
 					}
 				}
 			}
@@ -580,6 +632,7 @@ func getProjectItemFieldValue(itemID string, projectID int, fieldName string) (s
 						Number *float64 `json:"number,omitempty"`
 						Text   *string  `json:"text,omitempty"`
 						Name   *string  `json:"name,omitempty"`
+						Title  *string  `json:"title,omitempty"`
 					} `json:"nodes"`
 				} `json:"fieldValues"`
 			} `json:"node"`
@@ -603,6 +656,9 @@ func getProjectItemFieldValue(itemID string, projectID int, fieldName string) (s
 			if fieldValue.Name != nil {
 				return *fieldValue.Name, nil
 			}
+			if fieldValue.Title != nil {
+				return *fieldValue.Title, nil
+			}
 		}
 	}
 
@@ -707,3 +763,170 @@ func getCurrentIterationID(projectNodeID, fieldID string) (string, error) {
 
 	return "", fmt.Errorf("no iterations found for field")
 }
+
+// getCurrentIterationDetails returns ID, startDate (YYYY-MM-DD), and duration (days) for the current iteration.
+func getCurrentIterationDetails(projectNodeID, fieldID string) (string, string, int, error) {
+	// Same query shape as getCurrentIterationID
+	query := fmt.Sprintf(`{
+		node(id: "%s") {
+			... on ProjectV2 {
+				fields(first: 20) {
+					nodes {
+						... on ProjectV2IterationField {
+							id
+							name
+							configuration {
+								iterations {
+									id
+									title
+									startDate
+									duration
+								}
+							}
+						}
+					}
+				}
+			}
+		}
+	}`, projectNodeID)
+
+	command := fmt.Sprintf(`gh api graphql -f query='%s'`, query)
+	output, err := RunCommandAndReturnOutput(command)
+	if err != nil {
+		return "", "", 0, fmt.Errorf("failed to query iterations: %v", err)
+	}
+
+	var response struct {
+		Data struct {
+			Node struct {
+				Fields struct {
+					Nodes []struct {
+						ID            string `json:"id"`
+						Name          string `json:"name"`
+						Configuration struct {
+							Iterations []struct {
+								ID        string `json:"id"`
+								Title     string `json:"title"`
+								StartDate string `json:"startDate"`
+								Duration  int    `json:"duration"`
+							} `json:"iterations"`
+						} `json:"configuration"`
+					} `json:"nodes"`
+				} `json:"fields"`
+			} `json:"node"`
+		} `json:"data"`
+	}
+	if err := json.Unmarshal(output, &response); err != nil {
+		return "", "", 0, fmt.Errorf("failed to parse iterations response: %v", err)
+	}
+	for _, field := range response.Data.Node.Fields.Nodes {
+		if field.ID == fieldID {
+			if len(field.Configuration.Iterations) > 0 {
+				it := field.Configuration.Iterations[0]
+				return it.ID, it.StartDate, it.Duration, nil
+			}
+		}
+	}
+	return "", "", 0, fmt.Errorf("no iterations found for field")
+}
+
+// computePrevStartDate takes an ISO date string (YYYY-MM-DD) and a duration in days and returns the previous
+// iteration start date in the same format.
+func computePrevStartDate(curStart string, duration int) (string, error) {
+	t, err := time.Parse("2006-01-02", strings.TrimSpace(curStart))
+	if err != nil {
+		return "", err
+	}
+	prev := t.AddDate(0, 0, -duration)
+	return prev.Format("2006-01-02"), nil
+}
+
+// getPreviousIterationID attempts to find the iteration ID immediately prior to the current one.
+// It relies on the ordering returned by the iteration field configuration. If a previous iteration
+// is not present in the returned list, this will return an error.
+func getPreviousIterationID(projectNodeID, fieldID string) (string, error) {
+	// Reuse the same query as getCurrentIterationID to retrieve iterations
+	query := fmt.Sprintf(`{
+		node(id: "%s") {
+			... on ProjectV2 {
+				fields(first: 20) {
+					nodes {
+						... on ProjectV2IterationField {
+							id
+							name
+							configuration {
+								iterations {
+									id
+									title
+									startDate
+									duration
+								}
+							}
+						}
+					}
+				}
+			}
+		}
+	}`, projectNodeID)
+
+	command := fmt.Sprintf(`gh api graphql -f query='%s'`, query)
+	output, err := RunCommandAndReturnOutput(command)
+	if err != nil {
+		return "", fmt.Errorf("failed to query iterations: %v", err)
+	}
+	logger.Debugf("Iterations query response (previous): %s", string(output))
+
+	var response struct {
+		Data struct {
+			Node struct {
+				Fields struct {
+					Nodes []struct {
+						ID            string `json:"id"`
+						Name          string `json:"name"`
+						Configuration struct {
+							Iterations []struct {
+								ID        string `json:"id"`
+								Title     string `json:"title"`
+								StartDate string `json:"startDate"`
+								Duration  int    `json:"duration"`
+							} `json:"iterations"`
+						} `json:"configuration"`
+					} `json:"nodes"`
+				} `json:"fields"`
+			} `json:"node"`
+		} `json:"data"`
+	}
+
+	if err := json.Unmarshal(output, &response); err != nil {
+		return "", fmt.Errorf("failed to parse iterations response: %v", err)
+	}
+
+	var targetField *struct {
+		ID            string `json:"id"`
+		Name          string `json:"name"`
+		Configuration struct {
+			Iterations []struct {
+				ID        string `json:"id"`
+				Title     string `json:"title"`
+				StartDate string `json:"startDate"`
+				Duration  int    `json:"duration"`
+			} `json:"iterations"`
+		} `json:"configuration"`
+	}
+	for _, field := range response.Data.Node.Fields.Nodes {
+		if field.ID == fieldID {
+			targetField = &field
+			break
+		}
+	}
+	if targetField == nil {
+		return "", fmt.Errorf("iteration field with ID %s not found", fieldID)
+	}
+
+	iters := targetField.Configuration.Iterations
+	if len(iters) >= 2 {
+		logger.Infof("Selected previous iteration: %s (ID: %s)", iters[1].Title, iters[1].ID)
+		return iters[1].ID, nil
+	}
+	return "", fmt.Errorf("no previous iteration available")
+}
diff --git a/tools/github-manage/pkg/ghapi/projects_test.go b/tools/github-manage/pkg/ghapi/projects_test.go
index 3d8bcf8e2b..9d768a97b1 100644
--- a/tools/github-manage/pkg/ghapi/projects_test.go
+++ b/tools/github-manage/pkg/ghapi/projects_test.go
@@ -124,14 +124,16 @@ func TestParseJSONtoProjectItems(t *testing.T) {
 
 func TestAliases(t *testing.T) {
 	expectedAliases := map[string]int{
-		"mdm":             58,
-		"g-mdm":           58,
-		"draft":           67,
-		"drafting":        67,
-		"g-software":      70,
-		"soft":            70,
-		"g-orchestration": 71,
-		"orch":            71,
+		"mdm":                   58,
+		"g-mdm":                 58,
+		"draft":                 67,
+		"drafting":              67,
+		"g-software":            70,
+		"soft":                  70,
+		"g-orchestration":       71,
+		"orch":                  71,
+		"sec":                   97,
+		"g-security-compliance": 97,
 	}
 
 	if !reflect.DeepEqual(Aliases, expectedAliases) {
diff --git a/tools/github-manage/pkg/ghapi/workflows.go b/tools/github-manage/pkg/ghapi/workflows.go
index 7793d624e9..2c142b1167 100644
--- a/tools/github-manage/pkg/ghapi/workflows.go
+++ b/tools/github-manage/pkg/ghapi/workflows.go
@@ -1,6 +1,10 @@
 package ghapi
 
-import "fleetdm/gm/pkg/logger"
+import (
+	"strings"
+
+	"fleetdm/gm/pkg/logger"
+)
 
 // ActionType represents the type of action to be performed on an issue.
 type ActionType string
@@ -127,6 +131,26 @@ func CreateBulkSetSprintAction(issues []Issue, projectID int) []Action {
 	return actions
 }
 
+// CreateBulkMoveToCurrentSprintIfNotReadyQA creates actions to set current sprint for issues whose
+// status does NOT contain "ready" or "qa" (case-insensitive) in the given project.
+func CreateBulkMoveToCurrentSprintIfNotReadyQA(issues []Issue, projectID int) []Action {
+	var filtered []Issue
+	for _, is := range issues {
+		s := strings.ToLower(strings.TrimSpace(is.Status))
+		if s == "" {
+			// No status -> include (move to current sprint)
+			filtered = append(filtered, is)
+			continue
+		}
+		if strings.Contains(s, "ready") || strings.Contains(s, "qa") {
+			// Skip statuses with ready or qa
+			continue
+		}
+		filtered = append(filtered, is)
+	}
+	return CreateBulkSetSprintAction(filtered, projectID)
+}
+
 func CreateBulkSprintKickoffActions(issues []Issue, sourceProjectID, projectID int) []Action {
 	logger.Infof("Creating sprint kickoff actions for %d issues (source project: %d, target project: %d)", len(issues), sourceProjectID, projectID)
 
diff --git a/tools/github-manage/pkg/tui/hotkeys.go b/tools/github-manage/pkg/tui/hotkeys.go
index f9f9577388..eca3b5dc0d 100644
--- a/tools/github-manage/pkg/tui/hotkeys.go
+++ b/tools/github-manage/pkg/tui/hotkeys.go
@@ -244,7 +244,7 @@ func (m *model) HandleHotkeys(msg tea.Msg) (tea.Model, tea.Cmd) {
 					m.labelInput = ""
 				case BulkDemoSummary:
 					return m, m.executeWorkflow()
-				case BulkSprintKickoff, BulkKickOutOfSprint:
+				case BulkSprintKickoff, BulkKickOutOfSprint, BulkMoveToCurrentSprint:
 					if m.projectID != 0 {
 						// Use the provided project ID
 						return m, m.executeWorkflow()
diff --git a/tools/github-manage/pkg/tui/state_change.go b/tools/github-manage/pkg/tui/state_change.go
index 72768897f3..5fac8a962f 100644
--- a/tools/github-manage/pkg/tui/state_change.go
+++ b/tools/github-manage/pkg/tui/state_change.go
@@ -35,6 +35,7 @@ func (m *model) HandleStateChange(msg tea.Msg) (tea.Model, tea.Cmd) {
 		// Update viewport size when window is resized
 		m.detailViewport.Width = msg.Width - 4
 		m.detailViewport.Height = msg.Height - 6
+		m.termWidth = msg.Width
 	case processTaskMsg:
 		// This case is no longer used since we've moved to AsyncManager
 		// Ignore these messages
diff --git a/tools/github-manage/pkg/tui/ui.go b/tools/github-manage/pkg/tui/ui.go
index 7b1f93c55f..a9c68b7eb2 100644
--- a/tools/github-manage/pkg/tui/ui.go
+++ b/tools/github-manage/pkg/tui/ui.go
@@ -50,6 +50,7 @@ const (
 	BulkMilestoneClose
 	BulkKickOutOfSprint
 	BulkDemoSummary
+	BulkMoveToCurrentSprint
 )
 
 var WorkflowTypeValues = []string{
@@ -59,6 +60,7 @@ var WorkflowTypeValues = []string{
 	"Bulk Milestone Close",
 	"Bulk Kick Out Of Sprint",
 	"Bulk Demo Summary",
+	"Move to current sprint",
 }
 
 type TaskStatus int
@@ -137,6 +139,8 @@ type model struct {
 	detailViewport  viewport.Model
 	glamourRenderer *glamour.TermRenderer
 	issueContent    string
+	// Terminal sizing
+	termWidth int
 	// Command-specific parameters
 	commandType CommandType
 	projectID   int
@@ -203,6 +207,8 @@ func RunTUI(commandType CommandType, projectID int, limit int, search string) {
 		fmt.Println("Unsupported command type for TUI")
 		return
 	}
+	// Carry over the search string as a generic mode hint (e.g., for sprint: "previous")
+	mm.search = search
 	p := tea.NewProgram(&mm)
 	if _, err := p.Run(); err != nil {
 		fmt.Printf("Error running Bubble Tea program: %v\n", err)
@@ -343,6 +349,17 @@ func fetchSprintItems(projectID, limit int) tea.Cmd {
 	}
 }
 
+func fetchPreviousSprintItems(projectID, limit int) tea.Cmd {
+	return func() tea.Msg {
+		items, total, err := ghapi.GetPreviousSprintItemsWithTotal(projectID, limit)
+		if err != nil {
+			return err
+		}
+		issues := ghapi.ConvertItemsToIssues(items)
+		return issuesLoadedMsg{issues: issues, totalAvailable: total, rawFetched: limit}
+	}
+}
+
 // newview add command type / fetcher to switch
 func (m model) Init() tea.Cmd {
 	var fetchCmd tea.Cmd
@@ -354,7 +371,12 @@ func (m model) Init() tea.Cmd {
 	case EstimatedCommand:
 		fetchCmd = fetchEstimatedItems(m.projectID, m.limit)
 	case SprintCommand:
-		fetchCmd = fetchSprintItems(m.projectID, m.limit)
+		// Use the search field as a mode hint; when "previous", fetch previous sprint instead of current
+		if strings.EqualFold(strings.TrimSpace(m.search), "previous") || strings.EqualFold(strings.TrimSpace(m.search), "prev") {
+			fetchCmd = fetchPreviousSprintItems(m.projectID, m.limit)
+		} else {
+			fetchCmd = fetchSprintItems(m.projectID, m.limit)
+		}
 	default:
 		fetchCmd = fetchIssues("")
 	}
@@ -735,6 +757,39 @@ func (m *model) executeWorkflow() tea.Cmd {
 				Progress:    0.0,
 			})
 		}
+	case BulkMoveToCurrentSprint:
+		projectID := m.projectID
+		if projectID == 0 && m.projectInput != "" {
+			resolvedID, err := ghapi.ResolveProjectID(m.projectInput)
+			if err != nil {
+				return func() tea.Msg {
+					return workflowCompleteMsg{
+						success: false,
+						message: fmt.Sprintf("Failed to resolve project ID: %v", err),
+					}
+				}
+			}
+			projectID = resolvedID
+		}
+		if projectID == 0 {
+			return func() tea.Msg {
+				return workflowCompleteMsg{
+					success: false,
+					message: "Project ID is required for this workflow",
+				}
+			}
+		}
+		actions = ghapi.CreateBulkMoveToCurrentSprintIfNotReadyQA(selectedIssues, projectID)
+		for i, issue := range selectedIssues {
+			// Only tasks for those that will be acted on; description indicates conditional nature
+			desc := fmt.Sprintf("If not 'ready' or 'qa', set current sprint for #%d in project %d", issue.Number, projectID)
+			m.tasks = append(m.tasks, WorkflowTask{
+				ID:          i,
+				Description: desc,
+				Status:      TaskPending,
+				Progress:    0.0,
+			})
+		}
 	}
 
 	// For all workflows, start async workflow
diff --git a/tools/github-manage/pkg/tui/view.go b/tools/github-manage/pkg/tui/view.go
index 6d79999d70..db8115a826 100644
--- a/tools/github-manage/pkg/tui/view.go
+++ b/tools/github-manage/pkg/tui/view.go
@@ -364,10 +364,124 @@ func (m model) RenderWorkflowSelection() string {
 		}
 		s += fmt.Sprintf("%s %s %s\n", cursor, selected, workflow)
 	}
-	s += "\nPress 'enter' to select, 'esc' to cancel.\n"
+	// Detailed description for the currently-selected workflow
+	s += "\nDescription:\n"
+	width := m.termWidth
+	if width <= 0 {
+		width = 80
+	}
+	// Add a small margin to avoid bumping screen edges
+	wrapWidth := width - 2
+	if wrapWidth < 20 {
+		wrapWidth = 20
+	}
+	s += wrapTextPreserveBullets(m.selectedWorkflowDescription(), wrapWidth)
+	s += "\n\nPress 'enter' to select, 'esc' to cancel.\n"
 	return s
 }
 
+// selectedWorkflowDescription returns a helpful description for the currently-selected workflow,
+// including any required inputs and contextual hints.
+func (m model) selectedWorkflowDescription() string {
+	w := WorkflowType(m.workflowCursor)
+	// Base descriptions per workflow
+	var desc string
+	switch w {
+	case BulkAddLabel:
+		desc = "Add a label to all selected issues. You'll be prompted to type the label name."
+	case BulkRemoveLabel:
+		desc = "Remove a label from all selected issues. You'll be prompted to type the label name."
+	case BulkSprintKickoff:
+		desc = "Add selected issues to a project and set initial sprint kickoff fields (status, estimate sync, labels)."
+	case BulkMilestoneClose:
+		desc = "Generate a release summary from selected issues (features/bugs) suitable for milestone close notes."
+	case BulkKickOutOfSprint:
+		desc = "Remove selected issues from a project and reset sprint-related fields (status, labels)."
+	case BulkDemoSummary:
+		desc = "Generate a markdown summary of selected issues grouped by feature and bug, with assignees."
+	case BulkMoveToCurrentSprint:
+		desc = "For each selected issue, if its Status does not contain 'ready' or 'qa' (case-insensitive), set its sprint to the project's current iteration."
+	default:
+		desc = "Select a workflow to see details."
+	}
+
+	// Input requirements/hints
+	var hints []string
+	switch w {
+	case BulkAddLabel, BulkRemoveLabel:
+		hints = append(hints, "Input required: label name")
+	case BulkSprintKickoff, BulkKickOutOfSprint, BulkMoveToCurrentSprint:
+		hints = append(hints, "Input required: project ID or alias")
+		if m.projectID != 0 {
+			hints = append(hints, fmt.Sprintf("Current project in context: %d", m.projectID))
+		} else if m.projectInput != "" {
+			hints = append(hints, fmt.Sprintf("Pending project input: %s", m.projectInput))
+		}
+	}
+
+	if len(hints) > 0 {
+		desc += "\n- " + strings.Join(hints, "\n- ")
+	}
+	return desc
+}
+
+// wrapTextPreserveBullets wraps the input text to the given width, preserving
+// existing newlines and adding continuation indentation for bullet points.
+func wrapTextPreserveBullets(text string, width int) string {
+	if width <= 0 {
+		return text
+	}
+	lines := strings.Split(text, "\n")
+	var out []string
+	for _, line := range lines {
+		out = append(out, wrapLineWithPrefix(line, width))
+	}
+	return strings.Join(out, "\n")
+}
+
+// wrapLineWithPrefix wraps a single line. If it starts with "- ", it keeps
+// the bullet for the first line and indents continuation lines with two spaces.
+func wrapLineWithPrefix(line string, width int) string {
+	if len(line) <= width {
+		return line
+	}
+	bullet := ""
+	contIndent := ""
+	content := line
+	if strings.HasPrefix(line, "- ") {
+		bullet = "- "
+		contIndent = "  "
+		content = strings.TrimPrefix(line, "- ")
+	}
+	words := strings.Fields(content)
+	if len(words) == 0 {
+		return line
+	}
+	var wrapped []string
+	// first line with bullet (if any)
+	current := bullet
+	spaceLeft := width - len(current)
+	for _, w := range words {
+		if len(w)+1 > spaceLeft { // +1 for space
+			// commit current line
+			wrapped = append(wrapped, strings.TrimRight(current, " "))
+			// start new line with continuation indent
+			current = contIndent + w + " "
+			spaceLeft = width - len(contIndent) - len(w) - 1
+			if spaceLeft < 0 {
+				spaceLeft = 0
+			}
+		} else {
+			current += w + " "
+			spaceLeft -= len(w) + 1
+		}
+	}
+	if strings.TrimSpace(current) != "" {
+		wrapped = append(wrapped, strings.TrimRight(current, " "))
+	}
+	return strings.Join(wrapped, "\n")
+}
+
 func (m model) RenderLabelInput() string {
 	workflowName := "Add Label"
 	if m.workflowType == BulkRemoveLabel {