feat: Add PyPI dependency cooldown support (#221)

* refactor: Extract shared cooldown helpers to package-level functions

* feat: Add PyPI cooldown handler with PEP 691 file parsing

* feat: Add PyPI cooldown file stripping logic

* feat: Implement PyPI cooldown HandleMetadataRequest with PEP 691 filtering

* feat: Wire PyPI cooldown into pypi_registry interceptor

* update headers for no cache

* fix: Strip conditional GET headers to prevent 304 bypass in cooldown handlers

pip and npm clients cache Simple API / registry responses with ETags. On
subsequent requests they send If-None-Match, which causes the server to
return 304 Not Modified with no body. The cooldown response modifier
received an empty body, failed to parse it, and failed-open — letting
the client use its stale cached (unfiltered) response.

Fix: delete If-None-Match and If-Modified-Since from the request before
forwarding, forcing a full 200 response so the modifier always has a
body to filter.

Also removes the Content-Type guard from the PyPI modifier (the empty
Content-Type on 304 responses was a symptom of the same root cause) and
replaces Cache-Control: no-cache with the more targeted header deletion.

* docs: Add PyPI cooldown limitation for pip < 22.3 to dependency-cooldown docs

docs/dependency-cooldown.md

@@ -28,4 +28,12 @@ pmg --skip-dependency-cooldown npm install express
 
 ## Requirements
 
-Dependency cooldown requires [proxy mode](proxy-mode.md) to be enabled. It is currently supported for npm packages.
+Dependency cooldown requires [proxy mode](proxy-mode.md) to be enabled. It is supported for npm and PyPI packages.
+
+## Limitations
+
+### PyPI: requires pip 22.3+ or a PEP 691-capable client
+
+PyPI cooldown is enforced by filtering the [PEP 691 JSON Simple API](https://peps.python.org/pep-0691/) response, which includes a per-file `upload-time` field needed to determine when each version was published. This JSON format is only supported by pip 22.3+ (released October 2022) and other modern tools such as uv, Poetry, and PDM.
+
+Older pip versions request the HTML Simple API, which carries no publish timestamps. PMG cannot apply cooldown filtering to HTML responses and fails open; the request passes through unchanged and the client receives the full version list. Old pip gets no cooldown protection but does not break.

proxy/interceptors/cooldown.go

@@ -0,0 +1,48 @@
+package interceptors
+
+import "time"
+
+// cooldownIsWithinWindow reports whether a version published at publishDate is still
+// within the cooldown window of cooldownDays. Returns withinCooldown, daysSincePublish,
+// and daysRemaining.
+func cooldownIsWithinWindow(publishDate time.Time, cooldownDays int) (withinCooldown bool, daysSincePublish int, daysRemaining int) {
+	daysSincePublish = int(time.Since(publishDate).Hours() / 24)
+	if daysSincePublish < 0 {
+		daysSincePublish = 0
+	}
+	daysRemaining = cooldownDays - daysSincePublish
+	if daysRemaining < 0 {
+		daysRemaining = 0
+	}
+	return daysSincePublish < cooldownDays, daysSincePublish, daysRemaining
+}
+
+// cooldownOldestVersion returns the version with the earliest publish date.
+// When all versions are in cooldown, this is the one closest to exiting the window.
+func cooldownOldestVersion(dates map[string]time.Time) (string, time.Time) {
+	var oldest string
+	var oldestTime time.Time
+	for version, publishDate := range dates {
+		if oldestTime.IsZero() || publishDate.Before(oldestTime) {
+			oldest = version
+			oldestTime = publishDate
+		}
+	}
+	return oldest, oldestTime
+}
+
+// cooldownLatestEligibleVersion returns the most recently published version not in tooNew.
+func cooldownLatestEligibleVersion(dates map[string]time.Time, tooNew map[string]bool) string {
+	var latest string
+	var latestTime time.Time
+	for version, publishDate := range dates {
+		if tooNew[version] {
+			continue
+		}
+		if publishDate.After(latestTime) {
+			latest = version
+			latestTime = publishDate
+		}
+	}
+	return latest
+}

proxy/interceptors/cooldown_test.go

@@ -0,0 +1,164 @@
+package interceptors
+
+import (
+	"testing"
+	"time"
+
+	"github.com/stretchr/testify/assert"
+)
+
+func TestCooldownIsWithinWindow(t *testing.T) {
+	now := time.Now()
+	day := 24 * time.Hour
+
+	tests := []struct {
+		name                 string
+		publishDate          time.Time
+		cooldownDays         int
+		wantWithinCooldown   bool
+		wantDaysSincePublish int
+		wantDaysRemaining    int
+	}{
+		{
+			name:                 "published today with 30 day cooldown",
+			publishDate:          now,
+			cooldownDays:         30,
+			wantWithinCooldown:   true,
+			wantDaysSincePublish: 0,
+			wantDaysRemaining:    30,
+		},
+		{
+			name:                 "published exactly at cooldown boundary",
+			publishDate:          now.Add(-30 * day),
+			cooldownDays:         30,
+			wantWithinCooldown:   false,
+			wantDaysSincePublish: 30,
+			wantDaysRemaining:    0,
+		},
+		{
+			name:                 "published one day before cooldown expires",
+			publishDate:          now.Add(-29 * day),
+			cooldownDays:         30,
+			wantWithinCooldown:   true,
+			wantDaysSincePublish: 29,
+			wantDaysRemaining:    1,
+		},
+		{
+			name:                 "published well beyond cooldown",
+			publishDate:          now.Add(-365 * day),
+			cooldownDays:         30,
+			wantWithinCooldown:   false,
+			wantDaysSincePublish: 365,
+			wantDaysRemaining:    0,
+		},
+		{
+			name:                 "zero cooldown days",
+			publishDate:          now,
+			cooldownDays:         0,
+			wantWithinCooldown:   false,
+			wantDaysSincePublish: 0,
+			wantDaysRemaining:    0,
+		},
+		{
+			name:                 "future publish date clamped to zero days",
+			publishDate:          now.Add(5 * day),
+			cooldownDays:         30,
+			wantWithinCooldown:   true,
+			wantDaysSincePublish: 0,
+			wantDaysRemaining:    30,
+		},
+		{
+			name:                 "one day cooldown with publish today",
+			publishDate:          now,
+			cooldownDays:         1,
+			wantWithinCooldown:   true,
+			wantDaysSincePublish: 0,
+			wantDaysRemaining:    1,
+		},
+		{
+			name:                 "one day cooldown with publish yesterday",
+			publishDate:          now.Add(-1 * day),
+			cooldownDays:         1,
+			wantWithinCooldown:   false,
+			wantDaysSincePublish: 1,
+			wantDaysRemaining:    0,
+		},
+		{
+			name:                 "max int cooldown days does not overflow",
+			publishDate:          now.Add(-1 * day),
+			cooldownDays:         int(^uint(0) >> 1),
+			wantWithinCooldown:   true,
+			wantDaysSincePublish: 1,
+			wantDaysRemaining:    int(^uint(0)>>1) - 1,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			withinCooldown, daysSincePublish, daysRemaining := cooldownIsWithinWindow(tt.publishDate, tt.cooldownDays)
+			assert.Equal(t, tt.wantWithinCooldown, withinCooldown, "withinCooldown")
+			assert.Equal(t, tt.wantDaysSincePublish, daysSincePublish, "daysSincePublish")
+			assert.Equal(t, tt.wantDaysRemaining, daysRemaining, "daysRemaining")
+		})
+	}
+}
+
+func TestCooldownOldestVersion(t *testing.T) {
+	now := time.Now()
+	day := 24 * time.Hour
+
+	t.Run("returns version with earliest publish date", func(t *testing.T) {
+		dates := map[string]time.Time{
+			"1.0.0": now.Add(-30 * day),
+			"2.0.0": now.Add(-10 * day),
+			"3.0.0": now.Add(-1 * day),
+		}
+		ver, ts := cooldownOldestVersion(dates)
+		assert.Equal(t, "1.0.0", ver)
+		assert.False(t, ts.IsZero())
+	})
+
+	t.Run("single version", func(t *testing.T) {
+		dates := map[string]time.Time{"1.0.0": now.Add(-5 * day)}
+		ver, _ := cooldownOldestVersion(dates)
+		assert.Equal(t, "1.0.0", ver)
+	})
+
+	t.Run("empty map returns empty string and zero time", func(t *testing.T) {
+		ver, ts := cooldownOldestVersion(map[string]time.Time{})
+		assert.Empty(t, ver)
+		assert.True(t, ts.IsZero())
+	})
+}
+
+func TestCooldownLatestEligibleVersion(t *testing.T) {
+	now := time.Now()
+	day := 24 * time.Hour
+
+	t.Run("returns most recently published non-blocked version", func(t *testing.T) {
+		dates := map[string]time.Time{
+			"1.0.0": now.Add(-30 * day),
+			"2.0.0": now.Add(-10 * day),
+			"3.0.0": now.Add(-1 * day),
+		}
+		tooNew := map[string]bool{"3.0.0": true}
+		ver := cooldownLatestEligibleVersion(dates, tooNew)
+		assert.Equal(t, "2.0.0", ver)
+	})
+
+	t.Run("all versions blocked returns empty string", func(t *testing.T) {
+		dates := map[string]time.Time{"1.0.0": now, "2.0.0": now.Add(-1 * day)}
+		tooNew := map[string]bool{"1.0.0": true, "2.0.0": true}
+		ver := cooldownLatestEligibleVersion(dates, tooNew)
+		assert.Empty(t, ver)
+	})
+
+	t.Run("empty tooNew returns latest version", func(t *testing.T) {
+		dates := map[string]time.Time{
+			"1.0.0": now.Add(-30 * day),
+			"2.0.0": now.Add(-10 * day),
+		}
+		ver := cooldownLatestEligibleVersion(dates, map[string]bool{})
+		assert.Equal(t, "2.0.0", ver)
+	})
+}

proxy/interceptors/npm_cooldown.go

@@ -45,6 +45,13 @@ func (h *npmCooldownHandler) HandleMetadataRequest(ctx *proxy.RequestContext, pa
 	// we'd get raw gzip bytes that fail JSON parsing.
 	ctx.Headers.Set("Accept-Encoding", "identity")
 
+	// Strip conditional-GET headers so the registry cannot return 304 Not Modified.
+	// A 304 has no body — the modifier would receive an empty body, fail to parse
+	// it as JSON, and fail-open, letting the client use its cached (unfiltered)
+	// response. Removing these forces a full 200 response on every request.
+	ctx.Headers.Del("If-None-Match")
+	ctx.Headers.Del("If-Modified-Since")
+
 	modifier := func(statusCode int, headers http.Header, body []byte) (int, http.Header, []byte, error) {
 		dates, err := h.parseMetadataTime(body)
 		if err != nil {
@@ -60,9 +67,9 @@ func (h *npmCooldownHandler) HandleMetadataRequest(ctx *proxy.RequestContext, pa
 				ctx.RequestID, stripped, packageName, cooldownDays, remaining)
 
 			if remaining == 0 && h.statsCollector != nil {
-				oldestVer, oldestDate := h.oldestVersion(dates)
+				oldestVer, oldestDate := cooldownOldestVersion(dates)
 				if oldestVer != "" {
-					_, daysAgo, daysLeft := h.isWithinCooldown(oldestDate, cooldownDays)
+					_, daysAgo, daysLeft := cooldownIsWithinWindow(oldestDate, cooldownDays)
 					h.statsCollector.RecordCooldownBlocked(packageName, oldestVer, oldestDate, daysAgo, daysLeft, cooldownDays)
 				}
 			}
@@ -124,7 +131,7 @@ func (h *npmCooldownHandler) parseMetadataTime(body []byte) (map[string]time.Tim
 func (h *npmCooldownHandler) stripCooldownVersions(body []byte, dates map[string]time.Time, cooldownDays int) ([]byte, int, int) {
 	tooNew := make(map[string]bool)
 	for version, publishDate := range dates {
-		if withinCooldown, _, _ := h.isWithinCooldown(publishDate, cooldownDays); withinCooldown {
+		if withinCooldown, _, _ := cooldownIsWithinWindow(publishDate, cooldownDays); withinCooldown {
 			tooNew[version] = true
 		}
 	}
@@ -181,7 +188,7 @@ func (h *npmCooldownHandler) stripCooldownVersions(body []byte, dates map[string
 			changed := false
 			for tag, version := range distTags {
 				if tooNew[version] {
-					latest := h.latestNonCooldownVersion(dates, tooNew)
+					latest := cooldownLatestEligibleVersion(dates, tooNew)
 					if latest != "" {
 						distTags[tag] = latest
 					} else {
@@ -209,51 +216,3 @@ func (h *npmCooldownHandler) stripCooldownVersions(body []byte, dates map[string
 	return result, len(tooNew), remaining
 }
 
-// oldestVersion returns the version with the earliest publish date.
-// When all versions are blocked by cooldown, this is the version closest
-// to exiting the cooldown window (shortest wait for the user).
-func (h *npmCooldownHandler) oldestVersion(dates map[string]time.Time) (string, time.Time) {
-	var oldest string
-	var oldestTime time.Time
-
-	for version, publishDate := range dates {
-		if oldestTime.IsZero() || publishDate.Before(oldestTime) {
-			oldest = version
-			oldestTime = publishDate
-		}
-	}
-
-	return oldest, oldestTime
-}
-
-// isWithinCooldown reports whether a version published at publishDate is still
-// within the cooldown window of cooldownDays. It also returns the number of
-// whole days since publication.
-func (h *npmCooldownHandler) isWithinCooldown(publishDate time.Time, cooldownDays int) (withinCooldown bool, daysSincePublish int, daysRemaining int) {
-	daysSincePublish = int(time.Since(publishDate).Hours() / 24)
-	if daysSincePublish < 0 {
-		daysSincePublish = 0
-	}
-	daysRemaining = cooldownDays - daysSincePublish
-	if daysRemaining < 0 {
-		daysRemaining = 0
-	}
-	return daysSincePublish < cooldownDays, daysSincePublish, daysRemaining
-}
-
-func (h *npmCooldownHandler) latestNonCooldownVersion(dates map[string]time.Time, tooNew map[string]bool) string {
-	var latest string
-	var latestTime time.Time
-
-	for version, publishDate := range dates {
-		if tooNew[version] {
-			continue
-		}
-		if publishDate.After(latestTime) {
-			latest = version
-			latestTime = publishDate
-		}
-	}
-
-	return latest
-}

proxy/interceptors/npm_cooldown_test.go

@@ -298,12 +298,16 @@ func TestNpmCooldown_HandleMetadataRequest_OverridesHeaders(t *testing.T) {
 	ctx := makeTestRequestContext("https://registry.npmjs.org/lodash")
 	ctx.Headers.Set("Accept", "application/vnd.npm.install-v1+json")
 	ctx.Headers.Set("Accept-Encoding", "gzip")
+	ctx.Headers.Set("If-None-Match", `"abc123"`)
+	ctx.Headers.Set("If-Modified-Since", "Wed, 01 Jan 2025 00:00:00 GMT")
 
 	resp, err := handler.HandleMetadataRequest(ctx, "lodash", 5)
 	require.NoError(t, err)
 	assert.Equal(t, proxy.ActionModifyResponse, resp.Action)
 	assert.Equal(t, "application/json", ctx.Headers.Get("Accept"))
 	assert.Equal(t, "identity", ctx.Headers.Get("Accept-Encoding"))
+	assert.Empty(t, ctx.Headers.Get("If-None-Match"))
+	assert.Empty(t, ctx.Headers.Get("If-Modified-Since"))
 }
 
 func TestNpmCooldown_HandleMetadataRequest_StripsRecentVersions(t *testing.T) {
@@ -485,116 +489,3 @@ func TestNpmCooldown_TarballRequestBypassesCooldown(t *testing.T) {
 	// Accept header should not be set to application/json for tarball requests
 	assert.NotEqual(t, proxy.ActionModifyResponse, resp.Action)
 }
-
-func TestIsWithinCooldown(t *testing.T) {
-	h := newNpmCooldownHandler(nil)
-	now := time.Now()
-	day := 24 * time.Hour
-
-	tests := []struct {
-		name                 string
-		publishDate          time.Time
-		cooldownDays         int
-		wantWithinCooldown   bool
-		wantDaysSincePublish int
-		wantDaysRemaining    int
-	}{
-		{
-			name:                 "published today with 30 day cooldown",
-			publishDate:          now,
-			cooldownDays:         30,
-			wantWithinCooldown:   true,
-			wantDaysSincePublish: 0,
-			wantDaysRemaining:    30,
-		},
-		{
-			name:                 "published exactly at cooldown boundary",
-			publishDate:          now.Add(-30 * day),
-			cooldownDays:         30,
-			wantWithinCooldown:   false,
-			wantDaysSincePublish: 30,
-			wantDaysRemaining:    0,
-		},
-		{
-			name:                 "published one day before cooldown expires",
-			publishDate:          now.Add(-29 * day),
-			cooldownDays:         30,
-			wantWithinCooldown:   true,
-			wantDaysSincePublish: 29,
-			wantDaysRemaining:    1,
-		},
-		{
-			name:                 "published well beyond cooldown",
-			publishDate:          now.Add(-365 * day),
-			cooldownDays:         30,
-			wantWithinCooldown:   false,
-			wantDaysSincePublish: 365,
-			wantDaysRemaining:    0,
-		},
-		{
-			name:                 "zero cooldown days",
-			publishDate:          now,
-			cooldownDays:         0,
-			wantWithinCooldown:   false,
-			wantDaysSincePublish: 0,
-			wantDaysRemaining:    0,
-		},
-		{
-			name:                 "future publish date is clamped to zero days",
-			publishDate:          now.Add(5 * day),
-			cooldownDays:         30,
-			wantWithinCooldown:   true,
-			wantDaysSincePublish: 0,
-			wantDaysRemaining:    30,
-		},
-		{
-			name:                 "large cooldown days that previously caused overflow",
-			publishDate:          now.Add(-10 * day),
-			cooldownDays:         1000000,
-			wantWithinCooldown:   true,
-			wantDaysSincePublish: 10,
-			wantDaysRemaining:    999990,
-		},
-		{
-			name:                 "max int cooldown days does not overflow",
-			publishDate:          now.Add(-1 * day),
-			cooldownDays:         int(^uint(0) >> 1), // math.MaxInt
-			wantWithinCooldown:   true,
-			wantDaysSincePublish: 1,
-			wantDaysRemaining:    int(^uint(0)>>1) - 1,
-		},
-		{
-			name:                 "very old publish date well past cooldown",
-			publishDate:          now.Add(-3652 * day),
-			cooldownDays:         30,
-			wantWithinCooldown:   false,
-			wantDaysSincePublish: 3652,
-			wantDaysRemaining:    0,
-		},
-		{
-			name:                 "one day cooldown with publish yesterday",
-			publishDate:          now.Add(-1 * day),
-			cooldownDays:         1,
-			wantWithinCooldown:   false,
-			wantDaysSincePublish: 1,
-			wantDaysRemaining:    0,
-		},
-		{
-			name:                 "one day cooldown with publish today",
-			publishDate:          now,
-			cooldownDays:         1,
-			wantWithinCooldown:   true,
-			wantDaysSincePublish: 0,
-			wantDaysRemaining:    1,
-		},
-	}
-
-	for _, tt := range tests {
-		t.Run(tt.name, func(t *testing.T) {
-			withinCooldown, daysSincePublish, daysRemaining := h.isWithinCooldown(tt.publishDate, tt.cooldownDays)
-			assert.Equal(t, tt.wantWithinCooldown, withinCooldown, "withinCooldown")
-			assert.Equal(t, tt.wantDaysSincePublish, daysSincePublish, "daysSincePublish")
-			assert.Equal(t, tt.wantDaysRemaining, daysRemaining, "daysRemaining")
-		})
-	}
-}

proxy/interceptors/pypi_cooldown.go

@@ -0,0 +1,205 @@
+package interceptors
+
+import (
+	"encoding/json"
+	"fmt"
+	"net/http"
+	"time"
+
+	"github.com/safedep/dry/log"
+	"github.com/safedep/pmg/proxy"
+)
+
+const pypiSimpleAPIContentType = "application/vnd.pypi.simple.v1+json"
+
+// pypiCooldownHandler handles dependency cooldown for PyPI packages.
+// It strips recently-published file entries from PEP 691 Simple API responses
+// so pip's resolver naturally falls back to the latest eligible version.
+type pypiCooldownHandler struct {
+	statsCollector *AnalysisStatsCollector
+}
+
+func newPypiCooldownHandler(statsCollector *AnalysisStatsCollector) *pypiCooldownHandler {
+	return &pypiCooldownHandler{statsCollector: statsCollector}
+}
+
+// HandleMetadataRequest overrides the Accept header to force a PEP 691 JSON response,
+// then registers a response modifier that strips files for versions within the cooldown window.
+func (h *pypiCooldownHandler) HandleMetadataRequest(ctx *proxy.RequestContext, packageName string, cooldownDays int) (*proxy.InterceptorResponse, error) {
+	log.Debugf("[%s] Cooldown: registering metadata modifier for %s", ctx.RequestID, packageName)
+
+	// Force PEP 691 JSON so we receive upload-time per file entry.
+	ctx.Headers.Set("Accept", pypiSimpleAPIContentType)
+	// Prevent compression so the response body can be parsed as JSON directly.
+	ctx.Headers.Set("Accept-Encoding", "identity")
+	// Strip conditional-GET headers so PyPI cannot return 304 Not Modified.
+	// A 304 has no body — the modifier would receive an empty body, fail to parse
+	// it as JSON, and fail-open, letting the client use its cached (unfiltered)
+	// response. Removing these forces a full 200 response on every request.
+	ctx.Headers.Del("If-None-Match")
+	ctx.Headers.Del("If-Modified-Since")
+
+	modifier := func(statusCode int, headers http.Header, body []byte) (int, http.Header, []byte, error) {
+		dates, err := h.parsePEP691Files(body)
+		if err != nil {
+			log.Warnf("[%s] Cooldown: failed to parse PEP 691 metadata for %s: %v", ctx.RequestID, packageName, err)
+			return statusCode, headers, body, nil
+		}
+
+		log.Debugf("[%s] Cooldown: parsed %d versions for %s", ctx.RequestID, len(dates), packageName)
+
+		strippedBody, stripped, remaining := h.stripCooldownFiles(body, dates, cooldownDays)
+		if stripped > 0 {
+			log.Infof("[%s] Cooldown: stripped %d version(s) from %s metadata (%d days, %d eligible remain)",
+				ctx.RequestID, stripped, packageName, cooldownDays, remaining)
+
+			if remaining == 0 && h.statsCollector != nil {
+				oldestVer, oldestDate := cooldownOldestVersion(dates)
+				if oldestVer != "" {
+					_, daysAgo, daysLeft := cooldownIsWithinWindow(oldestDate, cooldownDays)
+					h.statsCollector.RecordCooldownBlocked(packageName, oldestVer, oldestDate, daysAgo, daysLeft, cooldownDays)
+				}
+			}
+
+			headers.Set("Cache-Control", "no-store")
+			return statusCode, headers, strippedBody, nil
+		}
+
+		return statusCode, headers, body, nil
+	}
+
+	return &proxy.InterceptorResponse{
+		Action:           proxy.ActionModifyResponse,
+		ResponseModifier: modifier,
+	}, nil
+}
+
+// parsePEP691Files extracts the earliest upload-time per version from a PEP 691 JSON body.
+// Files with missing or unparseable upload-time are skipped (treated as eligible).
+// Multiple files for the same version (sdist + wheels) use the earliest upload-time.
+func (h *pypiCooldownHandler) parsePEP691Files(body []byte) (map[string]time.Time, error) {
+	var resp struct {
+		Files []struct {
+			Filename   string `json:"filename"`
+			UploadTime string `json:"upload-time"`
+		} `json:"files"`
+	}
+
+	if err := json.Unmarshal(body, &resp); err != nil {
+		return nil, fmt.Errorf("failed to unmarshal PEP 691 response: %w", err)
+	}
+
+	dates := make(map[string]time.Time)
+	for _, f := range resp.Files {
+		if f.UploadTime == "" {
+			log.Debugf("Cooldown: skipping file %s with missing upload-time", f.Filename)
+			continue
+		}
+
+		t, err := parsePEP691UploadTime(f.UploadTime)
+		if err != nil {
+			log.Debugf("Cooldown: skipping file %s with unparseable upload-time %q: %v", f.Filename, f.UploadTime, err)
+			continue
+		}
+
+		pkgInfo, err := parseFilename(f.Filename)
+		if err != nil {
+			log.Debugf("Cooldown: skipping file %s with unparseable filename: %v", f.Filename, err)
+			continue
+		}
+
+		version := pkgInfo.GetVersion()
+		if version == "" {
+			continue
+		}
+
+		// Use the earliest upload-time across all files for a given version
+		if existing, ok := dates[version]; !ok || t.Before(existing) {
+			dates[version] = t
+		}
+	}
+
+	return dates, nil
+}
+
+// stripCooldownFiles removes all file entries for versions within the cooldown window
+// from a PEP 691 JSON body. Returns the modified body, number of versions stripped,
+// and number of versions remaining.
+func (h *pypiCooldownHandler) stripCooldownFiles(body []byte, dates map[string]time.Time, cooldownDays int) ([]byte, int, int) {
+	tooNew := make(map[string]bool)
+	for version, uploadDate := range dates {
+		if within, _, _ := cooldownIsWithinWindow(uploadDate, cooldownDays); within {
+			tooNew[version] = true
+		}
+	}
+
+	remaining := len(dates) - len(tooNew)
+
+	if len(tooNew) == 0 {
+		return body, 0, remaining
+	}
+
+	var resp map[string]json.RawMessage
+	if err := json.Unmarshal(body, &resp); err != nil {
+		log.Warnf("Cooldown: failed to unmarshal PEP 691 body for stripping: %v", err)
+		return body, 0, remaining
+	}
+
+	rawFiles, ok := resp["files"]
+	if !ok {
+		return body, 0, remaining
+	}
+
+	var files []json.RawMessage
+	if err := json.Unmarshal(rawFiles, &files); err != nil {
+		log.Warnf("Cooldown: failed to unmarshal files array: %v", err)
+		return body, 0, remaining
+	}
+
+	filtered := make([]json.RawMessage, 0, len(files))
+	for _, rawFile := range files {
+		var f struct {
+			Filename string `json:"filename"`
+		}
+		if err := json.Unmarshal(rawFile, &f); err != nil {
+			// Keep files we cannot parse to avoid accidentally dropping valid entries
+			filtered = append(filtered, rawFile)
+			continue
+		}
+
+		pkgInfo, err := parseFilename(f.Filename)
+		if err != nil {
+			// unparseable filename — keep it (fail-open)
+			filtered = append(filtered, rawFile)
+			continue
+		}
+		if tooNew[pkgInfo.GetVersion()] {
+			continue // strip
+		}
+		filtered = append(filtered, rawFile)
+	}
+
+	updatedFiles, err := json.Marshal(filtered)
+	if err != nil {
+		log.Warnf("Cooldown: failed to marshal filtered files array: %v", err)
+		return body, 0, remaining
+	}
+	resp["files"] = updatedFiles
+
+	result, err := json.Marshal(resp)
+	if err != nil {
+		log.Warnf("Cooldown: failed to marshal final PEP 691 response: %v", err)
+		return body, 0, remaining
+	}
+
+	return result, len(tooNew), remaining
+}
+
+// parsePEP691UploadTime parses the ISO 8601 upload-time field from PEP 691 responses.
+// Example: "2023-05-22T15:12:44.000000+00:00"
+func parsePEP691UploadTime(s string) (time.Time, error) {
+	if t, err := time.Parse(time.RFC3339Nano, s); err == nil {
+		return t, nil
+	}
+	return time.Parse(time.RFC3339, s)
+}

proxy/interceptors/pypi_cooldown_test.go

@@ -0,0 +1,559 @@
+package interceptors
+
+import (
+	"encoding/json"
+	"fmt"
+	"net/http"
+	"testing"
+	"time"
+
+	"github.com/safedep/pmg/config"
+	"github.com/safedep/pmg/proxy"
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+)
+
+// buildTestPEP691Response builds a PEP 691 JSON Simple API response for testing.
+// versions maps version string to upload time for a single .tar.gz file per version.
+func buildTestPEP691Response(versions map[string]time.Time) []byte {
+	type fileEntry struct {
+		Filename   string            `json:"filename"`
+		URL        string            `json:"url"`
+		UploadTime string            `json:"upload-time"`
+		Hashes     map[string]string `json:"hashes"`
+	}
+
+	files := make([]fileEntry, 0, len(versions))
+	for version, t := range versions {
+		files = append(files, fileEntry{
+			Filename:   fmt.Sprintf("testpkg-%s.tar.gz", version),
+			URL:        fmt.Sprintf("https://files.pythonhosted.org/packages/testpkg-%s.tar.gz", version),
+			UploadTime: t.UTC().Format(time.RFC3339Nano),
+			Hashes:     map[string]string{"sha256": "abc123"},
+		})
+	}
+
+	resp := map[string]any{
+		"meta":  map[string]string{"api-version": "1.0"},
+		"name":  "testpkg",
+		"files": files,
+	}
+	b, _ := json.Marshal(resp)
+	return b
+}
+
+func TestParsePEP691Files_ValidResponse(t *testing.T) {
+	handler := newPypiCooldownHandler(nil)
+	now := time.Now().UTC().Truncate(time.Second)
+	day := 24 * time.Hour
+
+	versions := map[string]time.Time{
+		"1.0.0": now.Add(-30 * day),
+		"2.0.0": now.Add(-10 * day),
+	}
+	body := buildTestPEP691Response(versions)
+
+	dates, err := handler.parsePEP691Files(body)
+	require.NoError(t, err)
+	assert.Len(t, dates, 2)
+	assert.Contains(t, dates, "1.0.0")
+	assert.Contains(t, dates, "2.0.0")
+}
+
+func TestParsePEP691Files_MultipleFilesPerVersion(t *testing.T) {
+	handler := newPypiCooldownHandler(nil)
+	now := time.Now().UTC().Truncate(time.Second)
+	day := 24 * time.Hour
+
+	// Two files for 1.0.0: sdist uploaded 5 days ago, wheel uploaded 3 days ago.
+	// parsePEP691Files must use the earliest (5 days ago).
+	sdistTime := now.Add(-5 * day)
+	wheelTime := now.Add(-3 * day)
+
+	body, _ := json.Marshal(map[string]any{
+		"meta": map[string]string{"api-version": "1.0"},
+		"name": "testpkg",
+		"files": []map[string]any{
+			{
+				"filename":    "testpkg-1.0.0.tar.gz",
+				"url":         "https://files.pythonhosted.org/packages/testpkg-1.0.0.tar.gz",
+				"upload-time": sdistTime.Format(time.RFC3339Nano),
+				"hashes":      map[string]string{"sha256": "abc"},
+			},
+			{
+				"filename":    "testpkg-1.0.0-py3-none-any.whl",
+				"url":         "https://files.pythonhosted.org/packages/testpkg-1.0.0-py3-none-any.whl",
+				"upload-time": wheelTime.Format(time.RFC3339Nano),
+				"hashes":      map[string]string{"sha256": "def"},
+			},
+		},
+	})
+
+	dates, err := handler.parsePEP691Files(body)
+	require.NoError(t, err)
+	require.Contains(t, dates, "1.0.0")
+	// Should use the earliest upload-time (sdist, 5 days ago)
+	assert.WithinDuration(t, sdistTime, dates["1.0.0"], time.Second)
+}
+
+func TestParsePEP691Files_MissingUploadTime(t *testing.T) {
+	handler := newPypiCooldownHandler(nil)
+
+	body, _ := json.Marshal(map[string]any{
+		"meta": map[string]string{"api-version": "1.0"},
+		"name": "testpkg",
+		"files": []map[string]any{
+			{
+				"filename": "testpkg-1.0.0.tar.gz",
+				"url":      "https://files.pythonhosted.org/packages/testpkg-1.0.0.tar.gz",
+				"hashes":   map[string]string{"sha256": "abc"},
+			},
+			{
+				"filename":    "testpkg-2.0.0.tar.gz",
+				"url":         "https://files.pythonhosted.org/packages/testpkg-2.0.0.tar.gz",
+				"upload-time": time.Now().Add(-10 * 24 * time.Hour).UTC().Format(time.RFC3339Nano),
+				"hashes":      map[string]string{"sha256": "def"},
+			},
+		},
+	})
+
+	dates, err := handler.parsePEP691Files(body)
+	require.NoError(t, err)
+	assert.NotContains(t, dates, "1.0.0")
+	assert.Contains(t, dates, "2.0.0")
+}
+
+func TestParsePEP691Files_YankedFiles(t *testing.T) {
+	handler := newPypiCooldownHandler(nil)
+	now := time.Now().UTC()
+
+	body, _ := json.Marshal(map[string]any{
+		"meta": map[string]string{"api-version": "1.0"},
+		"name": "testpkg",
+		"files": []map[string]any{
+			{
+				"filename":    "testpkg-1.0.0.tar.gz",
+				"url":         "https://files.pythonhosted.org/packages/testpkg-1.0.0.tar.gz",
+				"upload-time": now.Add(-2 * 24 * time.Hour).Format(time.RFC3339Nano),
+				"hashes":      map[string]string{"sha256": "abc"},
+				"yanked":      true,
+			},
+		},
+	})
+
+	dates, err := handler.parsePEP691Files(body)
+	require.NoError(t, err)
+	// Yanked file is still parsed — cooldown applies, pip handles yanked behaviour
+	assert.Contains(t, dates, "1.0.0")
+}
+
+func TestParsePEP691Files_InvalidJSON(t *testing.T) {
+	handler := newPypiCooldownHandler(nil)
+	_, err := handler.parsePEP691Files([]byte(`not-json`))
+	assert.Error(t, err)
+}
+
+func TestParsePEP691Files_EmptyFiles(t *testing.T) {
+	handler := newPypiCooldownHandler(nil)
+	body, _ := json.Marshal(map[string]any{
+		"meta":  map[string]string{"api-version": "1.0"},
+		"name":  "testpkg",
+		"files": []any{},
+	})
+
+	dates, err := handler.parsePEP691Files(body)
+	require.NoError(t, err)
+	assert.Empty(t, dates)
+}
+
+func TestStripCooldownFiles_MixedVersions(t *testing.T) {
+	handler := newPypiCooldownHandler(nil)
+	now := time.Now()
+	day := 24 * time.Hour
+
+	versions := map[string]time.Time{
+		"1.0.0": now.Add(-30 * day), // old — eligible
+		"2.0.0": now.Add(-1 * day),  // too new (5d cooldown)
+	}
+	body := buildTestPEP691Response(versions)
+
+	dates, err := handler.parsePEP691Files(body)
+	require.NoError(t, err)
+
+	newBody, stripped, remaining := handler.stripCooldownFiles(body, dates, 5)
+	assert.Equal(t, 1, stripped)
+	assert.Equal(t, 1, remaining)
+
+	var result struct {
+		Files []struct {
+			Filename string `json:"filename"`
+		} `json:"files"`
+	}
+	require.NoError(t, json.Unmarshal(newBody, &result))
+
+	filenames := make([]string, 0, len(result.Files))
+	for _, f := range result.Files {
+		filenames = append(filenames, f.Filename)
+	}
+	assert.Contains(t, filenames, "testpkg-1.0.0.tar.gz")
+	assert.NotContains(t, filenames, "testpkg-2.0.0.tar.gz")
+}
+
+func TestStripCooldownFiles_AllVersionsTooNew(t *testing.T) {
+	handler := newPypiCooldownHandler(nil)
+	now := time.Now()
+	day := 24 * time.Hour
+
+	versions := map[string]time.Time{
+		"1.0.0": now.Add(-1 * day),
+		"2.0.0": now.Add(-2 * day),
+	}
+	body := buildTestPEP691Response(versions)
+
+	dates, err := handler.parsePEP691Files(body)
+	require.NoError(t, err)
+
+	newBody, stripped, remaining := handler.stripCooldownFiles(body, dates, 5)
+	assert.Equal(t, 2, stripped)
+	assert.Equal(t, 0, remaining)
+
+	var result struct {
+		Files []json.RawMessage `json:"files"`
+	}
+	require.NoError(t, json.Unmarshal(newBody, &result))
+	assert.Empty(t, result.Files)
+}
+
+func TestStripCooldownFiles_NoVersionsTooNew(t *testing.T) {
+	handler := newPypiCooldownHandler(nil)
+	now := time.Now()
+	day := 24 * time.Hour
+
+	versions := map[string]time.Time{
+		"1.0.0": now.Add(-10 * day),
+		"2.0.0": now.Add(-20 * day),
+	}
+	body := buildTestPEP691Response(versions)
+
+	dates, err := handler.parsePEP691Files(body)
+	require.NoError(t, err)
+
+	newBody, stripped, remaining := handler.stripCooldownFiles(body, dates, 5)
+	assert.Equal(t, 0, stripped)
+	assert.Equal(t, 2, remaining)
+	assert.Equal(t, body, newBody)
+}
+
+func TestStripCooldownFiles_SingleVersionInCooldown(t *testing.T) {
+	handler := newPypiCooldownHandler(nil)
+	now := time.Now()
+
+	versions := map[string]time.Time{
+		"1.0.0": now.Add(-1 * 24 * time.Hour),
+	}
+	body := buildTestPEP691Response(versions)
+
+	dates, err := handler.parsePEP691Files(body)
+	require.NoError(t, err)
+
+	_, stripped, remaining := handler.stripCooldownFiles(body, dates, 5)
+	assert.Equal(t, 1, stripped)
+	assert.Equal(t, 0, remaining)
+}
+
+func TestStripCooldownFiles_MultipleFilesPerVersion_AllStripped(t *testing.T) {
+	handler := newPypiCooldownHandler(nil)
+	now := time.Now()
+
+	body, _ := json.Marshal(map[string]any{
+		"meta": map[string]string{"api-version": "1.0"},
+		"name": "testpkg",
+		"files": []map[string]any{
+			{
+				"filename":    "testpkg-1.0.0.tar.gz",
+				"url":         "https://files.pythonhosted.org/packages/testpkg-1.0.0.tar.gz",
+				"upload-time": now.Add(-1 * 24 * time.Hour).UTC().Format(time.RFC3339Nano),
+				"hashes":      map[string]string{"sha256": "abc"},
+			},
+			{
+				"filename":    "testpkg-1.0.0-py3-none-any.whl",
+				"url":         "https://files.pythonhosted.org/packages/testpkg-1.0.0-py3-none-any.whl",
+				"upload-time": now.Add(-2 * 24 * time.Hour).UTC().Format(time.RFC3339Nano),
+				"hashes":      map[string]string{"sha256": "def"},
+			},
+		},
+	})
+
+	dates, err := handler.parsePEP691Files(body)
+	require.NoError(t, err)
+
+	newBody, stripped, remaining := handler.stripCooldownFiles(body, dates, 5)
+	assert.Equal(t, 1, stripped)  // 1 version stripped
+	assert.Equal(t, 0, remaining)
+
+	var result struct {
+		Files []json.RawMessage `json:"files"`
+	}
+	require.NoError(t, json.Unmarshal(newBody, &result))
+	assert.Empty(t, result.Files) // both files (sdist + wheel) removed
+}
+
+func TestStripCooldownFiles_MalformedJSON(t *testing.T) {
+	handler := newPypiCooldownHandler(nil)
+	body := []byte(`not-json`)
+	dates := map[string]time.Time{"1.0.0": time.Now().Add(-1 * time.Hour)}
+
+	newBody, stripped, _ := handler.stripCooldownFiles(body, dates, 5)
+	assert.Equal(t, 0, stripped)
+	assert.Equal(t, body, newBody)
+}
+
+func TestStripCooldownFiles_UnparseableFilename_KeepFile(t *testing.T) {
+	handler := newPypiCooldownHandler(nil)
+	now := time.Now()
+
+	// .egg is an unsupported extension — parseFilename will fail
+	// The file must be kept (fail-open), not stripped
+	body, _ := json.Marshal(map[string]any{
+		"meta": map[string]string{"api-version": "1.0"},
+		"name": "testpkg",
+		"files": []map[string]any{
+			{
+				"filename":    "testpkg-1.0.0.egg",
+				"url":         "https://files.pythonhosted.org/packages/testpkg-1.0.0.egg",
+				"upload-time": now.Add(-1 * 24 * time.Hour).UTC().Format(time.RFC3339Nano),
+				"hashes":      map[string]string{"sha256": "abc"},
+			},
+		},
+	})
+
+	// parsePEP691Files will skip the .egg file (no version extracted),
+	// so dates will be empty — nothing to strip
+	dates, err := handler.parsePEP691Files(body)
+	require.NoError(t, err)
+	assert.Empty(t, dates)
+
+	// Force tooNew to include a version that matches nothing, to exercise the
+	// stripCooldownFiles path with a non-empty tooNew map
+	forcedDates := map[string]time.Time{
+		"1.0.0": now.Add(-1 * 24 * time.Hour),
+	}
+	newBody, stripped, _ := handler.stripCooldownFiles(body, forcedDates, 5)
+	assert.Equal(t, 1, stripped) // version is "stripped" from the date map perspective
+
+	var result struct {
+		Files []json.RawMessage `json:"files"`
+	}
+	require.NoError(t, json.Unmarshal(newBody, &result))
+	// The .egg file must still be present — unparseable filename means fail-open
+	assert.Len(t, result.Files, 1)
+}
+
+func TestPyPICooldown_HandleMetadataRequest_OverridesHeaders(t *testing.T) {
+	handler := newPypiCooldownHandler(nil)
+	ctx := makeTestRequestContext("https://pypi.org/simple/requests/")
+	ctx.Headers.Set("Accept", "text/html")
+	ctx.Headers.Set("Accept-Encoding", "gzip")
+	ctx.Headers.Set("If-None-Match", `"abc123"`)
+	ctx.Headers.Set("If-Modified-Since", "Wed, 01 Jan 2025 00:00:00 GMT")
+
+	resp, err := handler.HandleMetadataRequest(ctx, "requests", 5)
+	require.NoError(t, err)
+	assert.Equal(t, proxy.ActionModifyResponse, resp.Action)
+	assert.Equal(t, "application/vnd.pypi.simple.v1+json", ctx.Headers.Get("Accept"))
+	assert.Equal(t, "identity", ctx.Headers.Get("Accept-Encoding"))
+	assert.Empty(t, ctx.Headers.Get("If-None-Match"))
+	assert.Empty(t, ctx.Headers.Get("If-Modified-Since"))
+}
+
+func TestPyPICooldown_HandleMetadataRequest_NonJSONResponse_FailOpen(t *testing.T) {
+	handler := newPypiCooldownHandler(nil)
+	ctx := makeTestRequestContext("https://pypi.org/simple/requests/")
+
+	resp, err := handler.HandleMetadataRequest(ctx, "requests", 5)
+	require.NoError(t, err)
+	require.NotNil(t, resp.ResponseModifier)
+
+	htmlBody := []byte(`<!DOCTYPE html><html><body><a href="/packages/requests-2.31.0.tar.gz">requests-2.31.0.tar.gz</a></body></html>`)
+	headers := http.Header{}
+	headers.Set("Content-Type", "text/html")
+
+	_, retHeaders, retBody, err := resp.ResponseModifier(200, headers, htmlBody)
+	require.NoError(t, err)
+	assert.Equal(t, htmlBody, retBody)
+	assert.NotEqual(t, "no-store", retHeaders.Get("Cache-Control"))
+}
+
+func TestPyPICooldown_HandleMetadataRequest_StripsRecentVersions(t *testing.T) {
+	now := time.Now()
+	day := 24 * time.Hour
+	versions := map[string]time.Time{
+		"1.0.0": now.Add(-30 * day),
+		"2.0.0": now.Add(-1 * day),
+	}
+	body := buildTestPEP691Response(versions)
+
+	handler := newPypiCooldownHandler(NewAnalysisStatsCollector())
+	ctx := makeTestRequestContext("https://pypi.org/simple/testpkg/")
+
+	resp, err := handler.HandleMetadataRequest(ctx, "testpkg", 5)
+	require.NoError(t, err)
+	require.NotNil(t, resp.ResponseModifier)
+
+	headers := http.Header{}
+	headers.Set("Content-Type", "application/vnd.pypi.simple.v1+json")
+
+	_, retHeaders, retBody, err := resp.ResponseModifier(200, headers, body)
+	require.NoError(t, err)
+	assert.Equal(t, "no-store", retHeaders.Get("Cache-Control"))
+
+	var result struct {
+		Files []struct {
+			Filename string `json:"filename"`
+		} `json:"files"`
+	}
+	require.NoError(t, json.Unmarshal(retBody, &result))
+
+	filenames := make([]string, 0, len(result.Files))
+	for _, f := range result.Files {
+		filenames = append(filenames, f.Filename)
+	}
+	assert.Contains(t, filenames, "testpkg-1.0.0.tar.gz")
+	assert.NotContains(t, filenames, "testpkg-2.0.0.tar.gz")
+}
+
+func TestPyPICooldown_HandleMetadataRequest_AllVersionsInCooldown_RecordsStats(t *testing.T) {
+	now := time.Now()
+	versions := map[string]time.Time{
+		"1.0.0": now.Add(-1 * 24 * time.Hour),
+	}
+	body := buildTestPEP691Response(versions)
+
+	collector := NewAnalysisStatsCollector()
+	handler := newPypiCooldownHandler(collector)
+	ctx := makeTestRequestContext("https://pypi.org/simple/newpkg/")
+
+	resp, err := handler.HandleMetadataRequest(ctx, "newpkg", 5)
+	require.NoError(t, err)
+	require.NotNil(t, resp.ResponseModifier)
+
+	headers := http.Header{}
+	headers.Set("Content-Type", "application/vnd.pypi.simple.v1+json")
+
+	_, _, _, err = resp.ResponseModifier(200, headers, body)
+	require.NoError(t, err)
+
+	blocks := collector.GetCooldownBlocks()
+	require.Len(t, blocks, 1)
+	assert.Equal(t, "newpkg", blocks[0].Name)
+	assert.Equal(t, "1.0.0", blocks[0].Version)
+	assert.Equal(t, 5, blocks[0].CooldownDays)
+
+	stats := collector.GetStats()
+	assert.Equal(t, 1, stats.CooldownBlockedCount)
+	assert.Equal(t, 1, stats.BlockedCount)
+}
+
+func TestPyPICooldown_HandleMetadataRequest_NoVersionsInCooldown_BodyUnchanged(t *testing.T) {
+	now := time.Now()
+	day := 24 * time.Hour
+	versions := map[string]time.Time{
+		"1.0.0": now.Add(-30 * day),
+		"2.0.0": now.Add(-20 * day),
+	}
+	body := buildTestPEP691Response(versions)
+
+	handler := newPypiCooldownHandler(nil)
+	ctx := makeTestRequestContext("https://pypi.org/simple/testpkg/")
+
+	resp, err := handler.HandleMetadataRequest(ctx, "testpkg", 5)
+	require.NoError(t, err)
+	require.NotNil(t, resp.ResponseModifier)
+
+	headers := http.Header{}
+	headers.Set("Content-Type", "application/vnd.pypi.simple.v1+json")
+
+	_, _, retBody, err := resp.ResponseModifier(200, headers, body)
+	require.NoError(t, err)
+	assert.Equal(t, body, retBody)
+}
+
+func TestPyPICooldown_HandleMetadataRequest_MalformedJSON_FailOpen(t *testing.T) {
+	handler := newPypiCooldownHandler(nil)
+	ctx := makeTestRequestContext("https://pypi.org/simple/badpkg/")
+
+	resp, err := handler.HandleMetadataRequest(ctx, "badpkg", 5)
+	require.NoError(t, err)
+	require.NotNil(t, resp.ResponseModifier)
+
+	body := []byte(`not-json`)
+	headers := http.Header{}
+	headers.Set("Content-Type", "application/vnd.pypi.simple.v1+json")
+
+	_, _, retBody, err := resp.ResponseModifier(200, headers, body)
+	require.NoError(t, err)
+	assert.Equal(t, body, retBody)
+}
+
+func TestPyPICooldown_InterceptorDelegation_CooldownEnabled(t *testing.T) {
+	setCooldownConfig(t, config.DependencyCooldownConfig{Enabled: true, Days: 5})
+
+	interceptor := NewPypiRegistryInterceptor(nil, NewInMemoryAnalysisCache(), NewAnalysisStatsCollector(), make(chan *ConfirmationRequest, 1))
+
+	ctx := makeTestRequestContext("https://pypi.org/simple/requests/")
+	ctx.Hostname = "pypi.org"
+	ctx.Headers.Set("Accept", "text/html")
+
+	resp, err := interceptor.HandleRequest(ctx)
+	require.NoError(t, err)
+	assert.Equal(t, proxy.ActionModifyResponse, resp.Action)
+	assert.Equal(t, "application/vnd.pypi.simple.v1+json", ctx.Headers.Get("Accept"))
+}
+
+func TestPyPICooldown_InterceptorDelegation_CooldownDisabled(t *testing.T) {
+	setCooldownConfig(t, config.DependencyCooldownConfig{Enabled: false, Days: 5})
+
+	interceptor := NewPypiRegistryInterceptor(nil, NewInMemoryAnalysisCache(), NewAnalysisStatsCollector(), make(chan *ConfirmationRequest, 1))
+
+	ctx := makeTestRequestContext("https://pypi.org/simple/requests/")
+	ctx.Hostname = "pypi.org"
+	ctx.Headers.Set("Accept", "text/html")
+
+	resp, err := interceptor.HandleRequest(ctx)
+	require.NoError(t, err)
+	assert.Equal(t, proxy.ActionAllow, resp.Action)
+	assert.Equal(t, "text/html", ctx.Headers.Get("Accept"))
+}
+
+func TestPyPICooldown_JSONAPIRequest_NotIntercepted(t *testing.T) {
+	setCooldownConfig(t, config.DependencyCooldownConfig{Enabled: true, Days: 5})
+
+	interceptor := NewPypiRegistryInterceptor(nil, NewInMemoryAnalysisCache(), NewAnalysisStatsCollector(), make(chan *ConfirmationRequest, 1))
+
+	ctx := makeTestRequestContext("https://pypi.org/pypi/requests/json")
+	ctx.Hostname = "pypi.org"
+	ctx.Headers.Set("Accept", "application/json")
+
+	resp, err := interceptor.HandleRequest(ctx)
+	require.NoError(t, err)
+	assert.Equal(t, proxy.ActionAllow, resp.Action)
+	assert.Equal(t, "application/json", ctx.Headers.Get("Accept"))
+}
+
+func TestPyPICooldown_FileDownloadBypassesCooldown(t *testing.T) {
+	setCooldownConfig(t, config.DependencyCooldownConfig{Enabled: true, Days: 5})
+
+	origInsecure := config.Get().InsecureInstallation
+	config.Get().InsecureInstallation = true
+	t.Cleanup(func() { config.Get().InsecureInstallation = origInsecure })
+
+	interceptor := NewPypiRegistryInterceptor(nil, NewInMemoryAnalysisCache(), NewAnalysisStatsCollector(), make(chan *ConfirmationRequest, 1))
+
+	ctx := makeTestRequestContext("https://files.pythonhosted.org/packages/ab/cd/ef/requests-2.31.0-py3-none-any.whl")
+	ctx.Hostname = "files.pythonhosted.org"
+
+	resp, err := interceptor.HandleRequest(ctx)
+	require.NoError(t, err)
+	assert.NotEqual(t, proxy.ActionModifyResponse, resp.Action)
+	assert.NotEqual(t, "application/vnd.pypi.simple.v1+json", ctx.Headers.Get("Accept"))
+}

proxy/interceptors/pypi_registry.go

@@ -1,9 +1,12 @@
 package interceptors
 
 import (
+	"strings"
+
 	packagev1 "buf.build/gen/go/safedep/api/protocolbuffers/go/safedep/messages/package/v1"
 	"github.com/safedep/dry/log"
 	"github.com/safedep/pmg/analyzer"
+	pmgconfig "github.com/safedep/pmg/config"
 	"github.com/safedep/pmg/proxy"
 )
 
@@ -35,6 +38,7 @@ var pypiRegistryDomains = registryConfigMap{
 // It embeds baseRegistryInterceptor to reuse ecosystem agnostic functionality
 type PypiRegistryInterceptor struct {
 	baseRegistryInterceptor
+	cooldownHandler *pypiCooldownHandler
 }
 
 var _ proxy.Interceptor = (*PypiRegistryInterceptor)(nil)
@@ -55,6 +59,7 @@ func NewPypiRegistryInterceptor(
 			confirmationChan: confirmationChan,
 			circuitBreaker:   newAnalyzerCircuitBreaker("malysis-analyzer-pypi"),
 		},
+		cooldownHandler: newPypiCooldownHandler(statsCollector),
 	}
 }
 
@@ -105,9 +110,15 @@ func (i *PypiRegistryInterceptor) HandleRequest(ctx *proxy.RequestContext) (*pro
 		return &proxy.InterceptorResponse{Action: proxy.ActionAllow}, nil
 	}
 
-	// Only analyze actual file downloads (sdist or wheel)
-	// Metadata requests (Simple API or JSON API) are allowed through
 	if !pkgInfo.IsFileDownload() {
+		depCooldownConfig := pmgconfig.Get().Config.DependencyCooldown
+		// Only apply cooldown to Simple API requests (/simple/{pkg}/) — pip uses these
+		// for version resolution. JSON API requests (/pypi/{pkg}/json) are allowed through;
+		// they have a different response structure and pip does not use them for installs.
+		if depCooldownConfig.Enabled && strings.HasPrefix(ctx.URL.Path, "/simple/") {
+			return i.cooldownHandler.HandleMetadataRequest(ctx, pkgInfo.GetName(), depCooldownConfig.Days)
+		}
+
 		log.Debugf("[%s] Skipping analysis for metadata request: %s", ctx.RequestID, pkgInfo.GetName())
 		return &proxy.InterceptorResponse{Action: proxy.ActionAllow}, nil
 	}