diff --git a/internal/colorize/cropped.go b/internal/colorize/wrap.go
similarity index 79%
rename from internal/colorize/cropped.go
rename to internal/colorize/wrap.go
index 793a139513..74ca14e77b 100644
--- a/internal/colorize/cropped.go
+++ b/internal/colorize/wrap.go
@@ -5,14 +5,14 @@ import (
 	"strings"
 )
 
-type CroppedLines []CroppedLine
+type WrappedLines []WrappedLine
 
-type CroppedLine struct {
+type WrappedLine struct {
 	Line   string
 	Length int
 }
 
-func (c CroppedLines) String() string {
+func (c WrappedLines) String() string {
 	var result string
 	for _, crop := range c {
 		result = result + crop.Line
@@ -22,8 +22,9 @@ func (c CroppedLines) String() string {
 }
 
 var indentRegexp = regexp.MustCompile(`^([ ]+)`)
+var isLinkRegexp = regexp.MustCompile(`\s*(\[[^\]]+\])?https?://`)
 
-func GetCroppedText(text string, maxLen int, includeLineEnds bool) CroppedLines {
+func Wrap(text string, maxLen int, includeLineEnds bool, continuation string) WrappedLines {
 	indent := ""
 	if indentMatch := indentRegexp.FindStringSubmatch(text); indentMatch != nil {
 		indent = indentMatch[0]
@@ -32,11 +33,13 @@ func GetCroppedText(text string, maxLen int, includeLineEnds bool) CroppedLines
 		}
 	}
 
-	entries := make([]CroppedLine, 0)
+	maxLen -= len(continuation)
+
+	entries := make([]WrappedLine, 0)
 	colorCodes := colorRx.FindAllStringSubmatchIndex(text, -1)
 
 	isLineEnd := false
-	entry := CroppedLine{}
+	entry := WrappedLine{}
 	for pos, amend := range text {
 		inColorTag := inRange(pos, colorCodes)
 
@@ -69,8 +72,8 @@ func GetCroppedText(text string, maxLen int, includeLineEnds bool) CroppedLines
 					}
 				}
 				// Extract the word from the current line if it doesn't start the line.
-				if i > 0 && i < len(entry.Line)-1 {
-					wrapped = indent + entry.Line[i:]
+				if i > 0 && i < len(entry.Line)-1 && !isLinkRegexp.MatchString(entry.Line[i:]) {
+					wrapped = indent + continuation + entry.Line[i:]
 					entry.Line = entry.Line[:i]
 					entry.Length -= wrappedLength
 					isLineEnd = true // emulate for wrapping purposes
@@ -79,11 +82,11 @@ func GetCroppedText(text string, maxLen int, includeLineEnds bool) CroppedLines
 				}
 			}
 			entries = append(entries, entry)
-			entry = CroppedLine{Line: wrapped, Length: wrappedLength}
+			entry = WrappedLine{Line: wrapped, Length: wrappedLength}
 		}
 
 		if isLineEnd && includeLineEnds {
-			entries = append(entries, CroppedLine{"\n", 1})
+			entries = append(entries, WrappedLine{"\n", 1})
 		}
 	}
 
diff --git a/internal/colorize/cropped_test.go b/internal/colorize/wrap_test.go
similarity index 62%
rename from internal/colorize/cropped_test.go
rename to internal/colorize/wrap_test.go
index c16dac4544..f4d793c8a0 100644
--- a/internal/colorize/cropped_test.go
+++ b/internal/colorize/wrap_test.go
@@ -7,7 +7,7 @@ import (
 	"testing"
 )
 
-func Test_GetCroppedText(t *testing.T) {
+func Test_Wrap(t *testing.T) {
 	type args struct {
 		text   string
 		maxLen int
@@ -15,74 +15,74 @@ func Test_GetCroppedText(t *testing.T) {
 	tests := []struct {
 		name string
 		args args
-		want CroppedLines
+		want WrappedLines
 	}{
 		{
 			"No split",
 			args{"[HEADING]Hello[/RESET]", 5},
-			[]CroppedLine{{"[HEADING]Hello[/RESET]", 5}},
+			[]WrappedLine{{"[HEADING]Hello[/RESET]", 5}},
 		},
 		{
 			"Split",
 			args{"[HEADING]Hello[/RESET]", 3},
-			[]CroppedLine{{"[HEADING]Hel", 3}, {"lo[/RESET]", 2}},
+			[]WrappedLine{{"[HEADING]Hel", 3}, {"lo[/RESET]", 2}},
 		},
 		{
 			"Split multiple",
 			args{"[HEADING]Hello World[/RESET]", 3},
-			[]CroppedLine{{"[HEADING]Hel", 3}, {"lo ", 3}, {"Wor", 3}, {"ld[/RESET]", 2}},
+			[]WrappedLine{{"[HEADING]Hel", 3}, {"lo ", 3}, {"Wor", 3}, {"ld[/RESET]", 2}},
 		},
 		{
 			"Split multiple no match",
 			args{"Hello World", 3},
-			[]CroppedLine{{"Hel", 3}, {"lo ", 3}, {"Wor", 3}, {"ld", 2}},
+			[]WrappedLine{{"Hel", 3}, {"lo ", 3}, {"Wor", 3}, {"ld", 2}},
 		},
 		{
 			"No split no match",
 			args{"Hello", 5},
-			[]CroppedLine{{"Hello", 5}},
+			[]WrappedLine{{"Hello", 5}},
 		},
 		{
 			"Split multi-byte characters",
 			args{"✔ol1✔ol2✔ol3", 4},
-			[]CroppedLine{{"✔ol1", 4}, {"✔ol2", 4}, {"✔ol3", 4}},
+			[]WrappedLine{{"✔ol1", 4}, {"✔ol2", 4}, {"✔ol3", 4}},
 		},
 		{
 			"No split multi-byte character with tags",
 			args{"[HEADING]✔ Some Text[/RESET]", 20},
-			[]CroppedLine{{"[HEADING]✔ Some Text[/RESET]", 11}},
+			[]WrappedLine{{"[HEADING]✔ Some Text[/RESET]", 11}},
 		},
 		{
 			"Split multi-byte character with tags",
 			args{"[HEADING]✔ Some Text[/RESET]", 6},
-			[]CroppedLine{{"[HEADING]✔ Some", 6}, {" Text[/RESET]", 5}},
+			[]WrappedLine{{"[HEADING]✔ Some", 6}, {" Text[/RESET]", 5}},
 		},
 		{
 			"Split multi-byte character with tags by words",
 			args{"[HEADING]✔ Some Text[/RESET]", 10},
-			[]CroppedLine{{"[HEADING]✔ Some ", 7}, {"Text[/RESET]", 4}},
+			[]WrappedLine{{"[HEADING]✔ Some ", 7}, {"Text[/RESET]", 4}},
 		},
 		{
 			"Split line break",
 			args{"[HEADING]Hel\nlo[/RESET]", 5},
-			[]CroppedLine{{"[HEADING]Hel", 3}, {"lo[/RESET]", 2}},
+			[]WrappedLine{{"[HEADING]Hel", 3}, {"lo[/RESET]", 2}},
 		},
 		{
 			"Split nested",
 			args{"[HEADING][NOTICE]Hello[/RESET][/RESET]", 3},
-			[]CroppedLine{{"[HEADING][NOTICE]Hel", 3}, {"lo[/RESET][/RESET]", 2}},
+			[]WrappedLine{{"[HEADING][NOTICE]Hel", 3}, {"lo[/RESET][/RESET]", 2}},
 		},
 	}
 	for _, tt := range tests {
 		t.Run(tt.name, func(t *testing.T) {
-			if got := GetCroppedText(tt.args.text, tt.args.maxLen, false); !reflect.DeepEqual(got, tt.want) {
-				t.Errorf("getCroppedText() = %v, want %v", got, tt.want)
+			if got := Wrap(tt.args.text, tt.args.maxLen, false, ""); !reflect.DeepEqual(got, tt.want) {
+				t.Errorf("Wrap() = %v, want %v", got, tt.want)
 			}
 		})
 	}
 }
 
-func Test_GetCroppedTextAsString(t *testing.T) {
+func Test_WrapAsString(t *testing.T) {
 	tests := []struct {
 		name string
 		text string
@@ -119,11 +119,11 @@ func Test_GetCroppedTextAsString(t *testing.T) {
 	}
 	for _, tt := range tests {
 		t.Run(tt.name, func(t *testing.T) {
-			if got := GetCroppedText(tt.text, 999, true); !reflect.DeepEqual(got.String(), tt.text) {
+			if got := Wrap(tt.text, 999, true, ""); !reflect.DeepEqual(got.String(), tt.text) {
 				escape := func(v string) string {
 					return strings.Replace(v, "\n", "\\n", -1)
 				}
-				t.Errorf("getCroppedText() = %v, want %v (crop data: %s)", escape(got.String()), escape(tt.text), escape(fmt.Sprintf("%#v", got)))
+				t.Errorf("Wrap() = %v, want %v (crop data: %s)", escape(got.String()), escape(tt.text), escape(fmt.Sprintf("%#v", got)))
 			}
 		})
 	}
diff --git a/internal/output/plain.go b/internal/output/plain.go
index 3859303cf9..a927ced6f1 100644
--- a/internal/output/plain.go
+++ b/internal/output/plain.go
@@ -103,7 +103,7 @@ func (f *Plain) write(writer io.Writer, value interface{}) {
 // writeNow is a little helper that just writes the given value to the requested writer (no marshalling)
 func (f *Plain) writeNow(writer io.Writer, value string) {
 	if f.Config().Interactive {
-		value = wordWrap(value)
+		value = colorize.Wrap(value, termutils.GetWidth(), true, "").String()
 	}
 	_, err := colorize.Colorize(value, writer, !f.cfg.Colored)
 	if err != nil {
@@ -111,14 +111,6 @@ func (f *Plain) writeNow(writer io.Writer, value string) {
 	}
 }
 
-func wordWrap(text string) string {
-	return wordWrapWithWidth(text, termutils.GetWidth())
-}
-
-func wordWrapWithWidth(text string, width int) string {
-	return colorize.GetCroppedText(text, width, true).String()
-}
-
 const nilText = "<nil>"
 
 // sprint will marshal and return the given value as a string
diff --git a/internal/output/renderers/bulletlist.go b/internal/output/renderers/bulletlist.go
new file mode 100644
index 0000000000..947013a5d0
--- /dev/null
+++ b/internal/output/renderers/bulletlist.go
@@ -0,0 +1,89 @@
+package renderers
+
+import (
+	"fmt"
+	"strings"
+
+	"github.com/ActiveState/cli/internal/colorize"
+	"github.com/ActiveState/cli/internal/multilog"
+	"github.com/ActiveState/cli/internal/output"
+	"github.com/ActiveState/cli/internal/termutils"
+)
+
+type bulletList struct {
+	prefix  string
+	items   []string
+	bullets []string
+}
+
+// BulletTree outputs a list like:
+//
+// ├─ one
+// ├─ two
+// │ wrapped
+// └─ three
+var BulletTree = []string{output.TreeMid, output.TreeMid, output.TreeLink, output.TreeEnd}
+
+// HeadedBulletTree outputs a list like:
+//
+// one
+// ├─ two
+// │ wrapped
+// └─ three
+var HeadedBulletTree = []string{"", output.TreeMid, output.TreeLink, output.TreeEnd}
+
+// NewBulletList returns a printable list of items prefixed with the given set of bullets.
+// The set of bullets should contain four items: the bullet for the first item (e.g. ""); the
+// bullet for each subsequent item (e.g. "├─"); the bullet for an item's wrapped lines, if any
+// (e.g. "│"); and the bullet for the last item (e.g. "└─").
+// The returned list can be passed to a plain printer. It should not be passed to a structured
+// printer.
+func NewBulletList(prefix string, bullets, items []string) *bulletList {
+	if len(bullets) != 4 {
+		multilog.Error("Invalid bullet list: 4 bullets required")
+		bullets = BulletTree
+	}
+	return &bulletList{prefix, items, bullets}
+}
+
+func (b *bulletList) MarshalOutput(format output.Format) interface{} {
+	out := make([]string, len(b.items))
+
+	// Determine the indentation of each item.
+	// If the prefix is pure indentation, then the indent is that prefix.
+	// If the prefix is not pure indentation, then the indent is the number of characters between
+	// the first non-space character and the end of the prefix.
+	// For example, both "* " and " * " have and indent of 2 because items should be indented to
+	// match the bullet item's left margin (note that wrapping will auto-indent to match the leading
+	// space in the second example).
+	indent := b.prefix
+	if nonIndent := strings.TrimLeft(b.prefix, " "); nonIndent != "" {
+		indent = strings.Repeat(" ", len(nonIndent))
+	}
+
+	for i, item := range b.items {
+		bullet := b.bullets[0]
+		if len(b.items) == 1 {
+			bullet = b.bullets[3] // special case list length of one; use last bullet
+		}
+
+		if i == 0 {
+			if bullet != "" {
+				bullet += " "
+			}
+			item = b.prefix + bullet + item
+		} else {
+			bullet = b.bullets[1]
+			continuation := indent + b.bullets[2] + " "
+			if i == len(b.items)-1 {
+				bullet = b.bullets[3] // this is the last item
+				continuation = " "
+			}
+			wrapped := colorize.Wrap(item, termutils.GetWidth()-len(indent), true, continuation).String()
+			item = fmt.Sprintf("%s%s %s", indent, bullet, wrapped)
+		}
+		out[i] = item
+	}
+
+	return strings.Join(out, "\n")
+}
diff --git a/internal/runbits/dependencies/changesummary.go b/internal/runbits/dependencies/changesummary.go
index 38720f40d1..75e9a760f6 100644
--- a/internal/runbits/dependencies/changesummary.go
+++ b/internal/runbits/dependencies/changesummary.go
@@ -9,6 +9,7 @@ import (
 	"github.com/ActiveState/cli/internal/locale"
 	"github.com/ActiveState/cli/internal/logging"
 	"github.com/ActiveState/cli/internal/output"
+	"github.com/ActiveState/cli/internal/output/renderers"
 	"github.com/ActiveState/cli/internal/sliceutils"
 	"github.com/ActiveState/cli/pkg/buildplan"
 )
@@ -107,12 +108,8 @@ func OutputChangeSummary(out output.Outputer, newBuildPlan *buildplan.BuildPlan,
 	//   └─ name@oldVersion → name@newVersion (Updated)
 	// depending on whether or not it has subdependencies, and whether or not showUpdatedPackages is
 	// `true`.
+	items := make([]string, len(directDependencies))
 	for i, ingredient := range directDependencies {
-		prefix := output.TreeMid
-		if i == len(directDependencies)-1 {
-			prefix = output.TreeEnd
-		}
-
 		// Retrieve runtime dependencies, and then filter out any dependencies that are common between all added ingredients.
 		runtimeDeps := ingredient.RuntimeDependencies(true)
 		runtimeDeps = runtimeDeps.Filter(func(i *buildplan.Ingredient) bool { _, ok := commonDependencies[i.IngredientID]; return !ok })
@@ -130,8 +127,9 @@ func OutputChangeSummary(out output.Outputer, newBuildPlan *buildplan.BuildPlan,
 			item = fmt.Sprintf("[ACTIONABLE]%s@%s[/RESET] → %s (%s)", oldVersion.Name, oldVersion.Version, item, locale.Tl("updated", "updated"))
 		}
 
-		out.Notice(fmt.Sprintf("  [DISABLED]%s[/RESET] %s", prefix, item))
+		items[i] = item
 	}
 
+	out.Notice(renderers.NewBulletList("  ", renderers.BulletTree, items))
 	out.Notice("") // blank line
 }
diff --git a/internal/runbits/dependencies/summary.go b/internal/runbits/dependencies/summary.go
index 33fc2f6a49..a9008ac3a5 100644
--- a/internal/runbits/dependencies/summary.go
+++ b/internal/runbits/dependencies/summary.go
@@ -7,6 +7,7 @@ import (
 
 	"github.com/ActiveState/cli/internal/locale"
 	"github.com/ActiveState/cli/internal/output"
+	"github.com/ActiveState/cli/internal/output/renderers"
 	"github.com/ActiveState/cli/pkg/buildplan"
 )
 
@@ -27,12 +28,8 @@ func OutputSummary(out output.Outputer, directDependencies buildplan.Artifacts)
 	out.Notice("") // blank line
 	out.Notice(locale.Tl("setting_up_dependencies", "  Setting up the following dependencies:"))
 
+	items := make([]string, len(ingredients))
 	for i, ingredient := range ingredients {
-		prefix := "  " + output.TreeMid
-		if i == len(ingredients)-1 {
-			prefix = "  " + output.TreeEnd
-		}
-
 		subDependencies := ingredient.RuntimeDependencies(true)
 		if _, isCommon := commonDependencies[ingredient.IngredientID]; !isCommon {
 			// If the ingredient is itself not a common sub-dependency; filter out any common sub dependencies so we don't
@@ -44,10 +41,9 @@ func OutputSummary(out output.Outputer, directDependencies buildplan.Artifacts)
 			subdepLocale = locale.Tl("summary_subdeps", "([ACTIONABLE]{{.V0}}[/RESET] sub-dependencies)", strconv.Itoa(numSubs))
 		}
 
-		item := fmt.Sprintf("[ACTIONABLE]%s@%s[/RESET] %s", ingredient.Name, ingredient.Version, subdepLocale)
-
-		out.Notice(fmt.Sprintf("[DISABLED]%s[/RESET] %s", prefix, item))
+		items[i] = fmt.Sprintf("[ACTIONABLE]%s@%s[/RESET] %s", ingredient.Name, ingredient.Version, subdepLocale)
 	}
 
+	out.Notice(renderers.NewBulletList("  ", renderers.BulletTree, items))
 	out.Notice("") // blank line
 }
diff --git a/internal/runners/artifacts/artifacts.go b/internal/runners/artifacts/artifacts.go
index 078d2668a1..6d28db8ab0 100644
--- a/internal/runners/artifacts/artifacts.go
+++ b/internal/runners/artifacts/artifacts.go
@@ -12,6 +12,7 @@ import (
 	"github.com/ActiveState/cli/internal/errs"
 	"github.com/ActiveState/cli/internal/locale"
 	"github.com/ActiveState/cli/internal/output"
+	"github.com/ActiveState/cli/internal/output/renderers"
 	"github.com/ActiveState/cli/internal/primer"
 	buildplanner_runbit "github.com/ActiveState/cli/internal/runbits/buildplanner"
 	"github.com/ActiveState/cli/pkg/buildplan"
@@ -204,9 +205,13 @@ func (b *Artifacts) outputPlain(out *StructuredOutput, fullID bool) error {
 		for _, artifact := range platform.Artifacts {
 			switch {
 			case len(artifact.Errors) > 0:
-				b.out.Print(fmt.Sprintf("  • %s ([ERROR]%s[/RESET])", artifact.Name, locale.T("artifact_status_failed")))
-				b.out.Print(fmt.Sprintf("    %s %s: [ERROR]%s[/RESET]", output.TreeMid, locale.T("artifact_status_failed_message"), strings.Join(artifact.Errors, ": ")))
-				b.out.Print(fmt.Sprintf("    %s %s: [ACTIONABLE]%s[/RESET]", output.TreeEnd, locale.T("artifact_status_failed_log"), artifact.LogURL))
+				b.out.Print(renderers.NewBulletList("  • ",
+					renderers.HeadedBulletTree,
+					[]string{
+						fmt.Sprintf("%s ([ERROR]%s[/RESET])", artifact.Name, locale.T("artifact_status_failed")),
+						fmt.Sprintf("%s: [ERROR]%s[/RESET]", locale.T("artifact_status_failed_message"), strings.Join(artifact.Errors, ": ")),
+						fmt.Sprintf("%s: [ACTIONABLE]%s[/RESET]", locale.T("artifact_status_failed_log"), artifact.LogURL),
+					}))
 				continue
 			case artifact.status == types.ArtifactSkipped:
 				b.out.Print(fmt.Sprintf("  • %s ([NOTICE]%s[/RESET])", artifact.Name, locale.T("artifact_status_skipped")))
@@ -228,9 +233,13 @@ func (b *Artifacts) outputPlain(out *StructuredOutput, fullID bool) error {
 		for _, artifact := range platform.Packages {
 			switch {
 			case len(artifact.Errors) > 0:
-				b.out.Print(fmt.Sprintf("    • %s ([ERROR]%s[/RESET])", artifact.Name, locale.T("artifact_status_failed")))
-				b.out.Print(fmt.Sprintf("      %s %s: [ERROR]%s[/RESET]", output.TreeMid, locale.T("artifact_status_failed_message"), strings.Join(artifact.Errors, ": ")))
-				b.out.Print(fmt.Sprintf("      %s %s: [ACTIONABLE]%s[/RESET]", output.TreeEnd, locale.T("artifact_status_failed_log"), artifact.LogURL))
+				b.out.Print(renderers.NewBulletList("    • ",
+					renderers.HeadedBulletTree,
+					[]string{
+						fmt.Sprintf("%s ([ERROR]%s[/RESET])", artifact.Name, locale.T("artifact_status_failed")),
+						fmt.Sprintf("%s: [ERROR]%s[/RESET]", locale.T("artifact_status_failed_message"), strings.Join(artifact.Errors, ": ")),
+						fmt.Sprintf("%s: [ACTIONABLE]%s[/RESET]", locale.T("artifact_status_failed_log"), artifact.LogURL),
+					}))
 				continue
 			case artifact.status == types.ArtifactSkipped:
 				b.out.Print(fmt.Sprintf("    • %s ([NOTICE]%s[/RESET])", artifact.Name, locale.T("artifact_status_skipped")))
diff --git a/internal/runners/cve/cve.go b/internal/runners/cve/cve.go
index 20f6e51116..f1f886307b 100644
--- a/internal/runners/cve/cve.go
+++ b/internal/runners/cve/cve.go
@@ -10,6 +10,7 @@ import (
 	"github.com/ActiveState/cli/internal/errs"
 	"github.com/ActiveState/cli/internal/locale"
 	"github.com/ActiveState/cli/internal/output"
+	"github.com/ActiveState/cli/internal/output/renderers"
 	"github.com/ActiveState/cli/internal/primer"
 	"github.com/ActiveState/cli/internal/runbits/rationalize"
 	"github.com/ActiveState/cli/pkg/localcommit"
@@ -193,17 +194,15 @@ func (rd *cveOutput) MarshalOutput(format output.Format) interface{} {
 			return false
 		})
 
+		items := make([]string, len(ap.Details))
 		for i, d := range ap.Details {
-			bar := output.TreeMid
-			if i == len(ap.Details)-1 {
-				bar = output.TreeEnd
-			}
 			severity := d.Severity
 			if severity == "CRITICAL" {
 				severity = fmt.Sprintf("[ERROR]%-10s[/RESET]", severity)
 			}
-			rd.output.Print(fmt.Sprintf("  %s %-10s [ACTIONABLE]%s[/RESET]", bar, severity, d.CveID))
+			items[i] = fmt.Sprintf("%-10s [ACTIONABLE]%s[/RESET]", severity, d.CveID)
 		}
+		rd.output.Print(renderers.NewBulletList("", renderers.BulletTree, items))
 		rd.output.Print("")
 	}
 
diff --git a/internal/table/table.go b/internal/table/table.go
index b609daa29f..56924766f1 100644
--- a/internal/table/table.go
+++ b/internal/table/table.go
@@ -180,9 +180,9 @@ func renderRow(providedColumns []string, colWidths []int) string {
 		widths[len(widths)-1] = mathutils.Total(colWidths[len(widths)-1:]...)
 	}
 
-	croppedColumns := []colorize.CroppedLines{}
+	croppedColumns := []colorize.WrappedLines{}
 	for n, column := range providedColumns {
-		croppedColumns = append(croppedColumns, colorize.GetCroppedText(column, widths[n]-(padding*2), false))
+		croppedColumns = append(croppedColumns, colorize.Wrap(column, widths[n]-(padding*2), false, ""))
 	}
 
 	var rendered = true