diff --git a/go.mod b/go.mod
index ecb263d09..7d2431be5 100644
--- a/go.mod
+++ b/go.mod
@@ -36,6 +36,7 @@ require (
 	github.com/hashicorp/go-version v1.9.0
 	github.com/iancoleman/strcase v0.3.0
 	github.com/joho/godotenv v1.5.1
+	github.com/muesli/reflow v0.3.0
 	github.com/pb33f/openapi-changes v0.0.63
 	github.com/pkg/errors v0.9.1
 	github.com/pmezard/go-difflib v1.0.1-0.20181226105442-5d4384ee4fb2
@@ -47,7 +48,7 @@ require (
 	github.com/speakeasy-api/huh v1.1.2
 	github.com/speakeasy-api/jq v0.13.0
 	github.com/speakeasy-api/openapi v1.25.0
-	github.com/speakeasy-api/openapi-generation/v2 v2.941.0
+	github.com/speakeasy-api/openapi-generation/v2 v2.943.0
 	github.com/speakeasy-api/sdk-gen-config v1.58.0
 	github.com/speakeasy-api/speakeasy-agent-mode-content v0.2.12
 	github.com/speakeasy-api/speakeasy-client-sdk-go/v3 v3.28.1
@@ -197,7 +198,6 @@ require (
 	github.com/moby/term v0.5.2 // indirect
 	github.com/muesli/ansi v0.0.0-20230316100256-276c6243b2f6 // indirect
 	github.com/muesli/cancelreader v0.2.2 // indirect
-	github.com/muesli/reflow v0.3.0 // indirect
 	github.com/muesli/termenv v0.16.0 // indirect
 	github.com/olekukonko/tablewriter v0.0.5 // indirect
 	github.com/opencontainers/go-digest v1.0.0 // indirect
diff --git a/go.sum b/go.sum
index 64409047f..5bbfd1bba 100644
--- a/go.sum
+++ b/go.sum
@@ -548,8 +548,8 @@ github.com/speakeasy-api/libopenapi v0.21.10-fixhiddencomps-fixed h1:ZtuakKtG6x7
 github.com/speakeasy-api/libopenapi v0.21.10-fixhiddencomps-fixed/go.mod h1:Gc8oQkjr2InxwumK0zOBtKN9gIlv9L2VmSVIUk2YxcU=
 github.com/speakeasy-api/openapi v1.25.0 h1:xyJ5ZzW4YwStT2ICo0o7v9M890J7VpsR7AqhQSZnwl4=
 github.com/speakeasy-api/openapi v1.25.0/go.mod h1:9gGkzi9jNspEbcB08zta+IjzAi5Zy4QgSEQfF/LSrbQ=
-github.com/speakeasy-api/openapi-generation/v2 v2.941.0 h1:ugKtFsX/lMvKF8omR+C9zhU0zkV2J64IwyIG64Eji3E=
-github.com/speakeasy-api/openapi-generation/v2 v2.941.0/go.mod h1:38+qTY7CB1YwaGT1VvwSTF23l3nHDx8wbjkBPig9S54=
+github.com/speakeasy-api/openapi-generation/v2 v2.943.0 h1:iR1Kb/7/O66wavfzyCPqoEJ0ejIDmyWZ/gRMfclPi98=
+github.com/speakeasy-api/openapi-generation/v2 v2.943.0/go.mod h1:38+qTY7CB1YwaGT1VvwSTF23l3nHDx8wbjkBPig9S54=
 github.com/speakeasy-api/openapi/openapi/linter/customrules v0.0.0-20260206023826-2483fb8e98b4 h1:gV+lYeVNNJG9X3Sl9Su3cRh1iF/oNqzvb5Ijq2QR8jY=
 github.com/speakeasy-api/openapi/openapi/linter/customrules v0.0.0-20260206023826-2483fb8e98b4/go.mod h1:1zQpVio7X6QJDtyNdUguCgZ+IC7CzKhhjvNgJdvGVF0=
 github.com/speakeasy-api/sdk-gen-config v1.58.0 h1:JrDgDU3XBIidv+TXFqYBvIomfeGEQ0zN+OnHyUc+kNw=
diff --git a/prompts/configs_test.go b/prompts/configs_test.go
index d01a2cfc5..52391e55a 100644
--- a/prompts/configs_test.go
+++ b/prompts/configs_test.go
@@ -29,9 +29,9 @@ func TestTargetSpecificForms_Ruby_Quickstart(t *testing.T) {
 	tm := charmtest.ModelFromHuhGroup(t, groups...)
 	tm.AssertContains(t,
 		"┃ Choose a packageName",
-		"┃ The distribution name of the Ruby Package.",
-		"https://guides.rubygems.org/name-",
-		"your-gem/",
+		"┃ The distribution name of the Ruby Package. https://guides.rubygems.org/name-your-gem/ Use a lowercase",
+		"┃ name: a name that differs from its snake_case form only by case gets no gem-name entry file, so",
+		"┃ Bundler will not autoload it on case-sensitive filesystems.",
 		"┃ openapi",
 	)
 	tm.SendKeys(tea.KeyEnter)
diff --git a/prompts/target_form_field.go b/prompts/target_form_field.go
index 2107cb8f9..2e2d1cbae 100644
--- a/prompts/target_form_field.go
+++ b/prompts/target_form_field.go
@@ -8,6 +8,7 @@ import (
 	"strings"
 
 	"github.com/iancoleman/strcase"
+	"github.com/muesli/reflow/wordwrap"
 	"github.com/speakeasy-api/huh"
 	config "github.com/speakeasy-api/sdk-gen-config"
 	"github.com/speakeasy-api/speakeasy/internal/charm"
@@ -215,9 +216,9 @@ func (f *TargetFormField) HuhField(targetFormFields TargetFormFields) huh.Field
 
 		if f.DescriptionFunc != nil {
 			fn := func() string {
-				return f.DescriptionFunc(*value)
+				return wordwrap.String(f.DescriptionFunc(*value), 100)
 			}
-			input = input.DescriptionFunc(fn, value).Inline(false).Prompt("")
+			input = input.Description(fn()).DescriptionFunc(fn, value).Inline(false).Prompt("")
 		}
 
 		if f.SuggestionsFunc != nil {
@@ -278,9 +279,9 @@ func (f *TargetFormField) HuhField(targetFormFields TargetFormFields) huh.Field
 
 			if f.DescriptionFunc != nil {
 				fn := func() string {
-					return f.DescriptionFunc(intValue)
+					return wordwrap.String(f.DescriptionFunc(intValue), 100)
 				}
-				input = input.DescriptionFunc(fn, &intValue).Inline(false).Prompt("")
+				input = input.Description(fn()).DescriptionFunc(fn, &intValue).Inline(false).Prompt("")
 			}
 
 			if f.SuggestionsFunc != nil {