diff --git a/internal/setup/setup.go b/internal/setup/setup.go
index 6ed24abe..23d0746f 100644
--- a/internal/setup/setup.go
+++ b/internal/setup/setup.go
@@ -3,6 +3,7 @@ package setup
 import (
 	"errors"
 	"fmt"
+	"maps"
 	"os"
 	"path/filepath"
 	"slices"
@@ -273,14 +274,46 @@ func (r *Release) validate() error {
 	}
 
 	// Check for glob and generate conflicts.
+	//
+	// This is the most time-consuming part of every command because checking
+	// each pair of paths uses an n^2 algorithm; specifically due to glob
+	// handling. We can speed up the process by exploiting the fact that
+	// conflicts are not allowed which means that in valid releases globs will
+	// appear at only the specific parts of the paths. There will always be a
+	// non-trivial prefix of the path that doesn't contain globs.
+	//
+	// We will speed up the search by only looking for conflicts in paths that
+	// share this same prefix. By collecting all paths and doing binary search
+	// we can find the start of the prefix. This is much simpler than other
+	// data structures like tries or radix trees which have similar algorithmic
+	// complexities.
+	allPaths := slices.Collect(maps.Keys(paths))
+	slices.Sort(allPaths)
 	for oldPath, oldSlices := range paths {
 		for _, old := range oldSlices {
 			oldInfo := old.Contents[oldPath]
 			if oldInfo.Kind != GeneratePath && oldInfo.Kind != GlobPath {
 				break
 			}
-			for newPath, newSlices := range paths {
-				if oldPath == newPath {
+
+			prefixLen := strings.IndexAny(oldPath, "*?")
+			if prefixLen == -1 {
+				return fmt.Errorf("internal error: invalid path: generate or glob path does not contain ' ?' or '*': %q", oldPath)
+			}
+			searchKey := oldPath[:prefixLen]
+			// startIndex is the position of the prefix or the position where
+			// the prefix would have been found.
+			startIndex, _ := slices.BinarySearch(allPaths, searchKey)
+			for i := startIndex; i < len(allPaths); i++ {
+				newPath := allPaths[i]
+				if !strings.HasPrefix(newPath, searchKey) {
+					// Iterate until the prefix no longer matches, which means
+					// all other paths will fail the comparison below.
+					break
+				}
+				newSlices := paths[newPath]
+				// We know prefixes match, we can skip that part of the string.
+				if oldPath[len(searchKey)-1:] == newPath[len(searchKey)-1:] {
 					// Identical paths have been filtered earlier.
 					continue
 				}
@@ -291,13 +324,16 @@ func (r *Release) validate() error {
 							continue
 						}
 					}
-					if strdist.GlobPath(newPath, oldPath) {
+					// We know prefixes match, we can skip that part of the string.
+					if strdist.GlobPath(newPath[len(searchKey)-1:], oldPath[len(searchKey)-1:]) {
 						if (old.Package > new.Package) || (old.Package == new.Package && old.Name > new.Name) ||
 							(old.Package == new.Package && old.Name == new.Name && oldPath > newPath) {
 							old, new = new, old
 							oldPath, newPath = newPath, oldPath
 						}
 						return fmt.Errorf("slices %s and %s conflict on %s and %s", old, new, oldPath, newPath)
+					} else {
+						break
 					}
 				}
 			}
diff --git a/internal/setup/setup_test.go b/internal/setup/setup_test.go
index d669943f..4456ce0b 100644
--- a/internal/setup/setup_test.go
+++ b/internal/setup/setup_test.go
@@ -518,6 +518,86 @@ var setupTests = []setupTest{{
 		`,
 	},
 	relerror: "slices mypkg1_myslice1 and mypkg2_myslice1 conflict on /path1",
+}, {
+	summary: "When multiple prefixes match all are tested",
+	input: map[string]string{
+		"slices/mydir/mypkg1.yaml": `
+			package: mypkg1
+			slices:
+				myslice1:
+					contents:
+						/path/*/foo:
+		`,
+		"slices/mydir/mypkg2.yaml": `
+			package: mypkg2
+			slices:
+				myslice1:
+					contents:
+						/path/bar/foo1:
+						/path/bar/f*:
+		`,
+	},
+	relerror: "slices mypkg1_myslice1 and mypkg2_myslice1 conflict on /path/\\*/foo and /path/bar/f\\*",
+}, {
+	summary: "Later matching paths are tested after several non-matches",
+	input: map[string]string{
+		"slices/mydir/mypkg1.yaml": `
+			package: mypkg1
+			slices:
+				myslice1:
+					contents:
+						/path/*/foo:
+		`,
+		"slices/mydir/mypkg2.yaml": `
+			package: mypkg2
+			slices:
+				myslice1:
+					contents:
+						/path/bar/f:
+						/path/bar/fa:
+						/path/bar/fb:
+						/path/bar/f*:
+		`,
+	},
+	relerror: "slices mypkg1_myslice1 and mypkg2_myslice1 conflict on /path/\\*/foo and /path/bar/f\\*",
+}, {
+	summary: "Conflicting globs with wildcard in the middle of the segment",
+	input: map[string]string{
+		"slices/mydir/mypkg1.yaml": `
+			package: mypkg1
+			slices:
+				myslice:
+					contents:
+						/path/ab*cd/file:
+		`,
+		"slices/mydir/mypkg2.yaml": `
+			package: mypkg2
+			slices:
+				myslice:
+					contents:
+						/path/ab12cd/file:
+		`,
+	},
+	relerror: `slices mypkg1_myslice and mypkg2_myslice conflict on /path/ab\*cd/file and /path/ab12cd/file`,
+}, {
+	summary: "Conflicting globs when one side uses double-star",
+	input: map[string]string{
+		"slices/mydir/mypkg1.yaml": `
+			package: mypkg1
+			slices:
+				myslice:
+					contents:
+						/path/**/file:
+		`,
+		"slices/mydir/mypkg2.yaml": `
+			package: mypkg2
+			slices:
+				myslice:
+					contents:
+						/path/*/file:
+		`,
+	},
+	relerror: `slices mypkg1_myslice and mypkg2_myslice conflict on /path/\*\*/file and /path/\*/file`,
 }, {
 	summary: "Directories must be suffixed with /",
 	input: map[string]string{
@@ -1943,6 +2023,25 @@ var setupTests = []setupTest{{
 		`,
 	},
 	relerror: `slices mypkg_myslice1 and mypkg_myslice2 conflict on /path/subdir/\*\* and /path/\*\*`,
+}, {
+	summary: "Generate paths conflict with glob paths sharing the prefix",
+	input: map[string]string{
+		"slices/mydir/mypkg1.yaml": `
+			package: mypkg1
+			slices:
+				myslice:
+					contents:
+						/path/subdir/**: {generate: manifest}
+		`,
+		"slices/mydir/mypkg2.yaml": `
+			package: mypkg2
+			slices:
+				myslice:
+					contents:
+						/path/subdir/f*:
+		`,
+	},
+	relerror: `slices mypkg1_myslice and mypkg2_myslice conflict on /path/subdir/\*\* and /path/subdir/f\*`,
 }, {
 	summary: `No other options in "generate" paths`,
 	input: map[string]string{
diff --git a/internal/strdist/strdist.go b/internal/strdist/strdist.go
index d5b640ef..baff1c38 100644
--- a/internal/strdist/strdist.go
+++ b/internal/strdist/strdist.go
@@ -34,14 +34,14 @@ func Distance(a, b string, f CostFunc, cut int64) int64 {
 	}
 	lst := make([]CostInt, len(b)+1)
 	bl := 0
-	for bi, br := range b {
-		bl++
+	for _, br := range b {
 		cost := f(-1, br)
-		if cost.InsertB == Inhibit || lst[bi] == Inhibit {
-			lst[bi+1] = Inhibit
+		if cost.InsertB == Inhibit || lst[bl] == Inhibit {
+			lst[bl+1] = Inhibit
 		} else {
-			lst[bi+1] = lst[bi] + cost.InsertB
+			lst[bl+1] = lst[bl] + cost.InsertB
 		}
+		bl++
 	}
 	lst = lst[:bl+1]
 	// Not required, but caching means preventing the fast path
@@ -87,8 +87,7 @@ func Distance(a, b string, f CostFunc, cut int64) int64 {
 		if debug {
 			debugf("... %v", lst)
 		}
-		_ = stop
-		if cut != 0 && stop {
+		if cut != 0 && len(b) > 0 && stop {
 			break
 		}
 	}
@@ -105,66 +104,96 @@ func Distance(a, b string, f CostFunc, cut int64) int64 {
 //	*  - Any zero or more characters, except for /
 //	** - Any zero or more characters, including /
 func GlobPath(a, b string) bool {
-	if !wildcardPrefixMatch(a, b) {
-		// Fast path.
-		return false
+	// Computing the actual distance is slow as its complexity is
+	// O(len(a) * len(b)). If the paths contain globs there is no way around
+	// it, but we can be clever about creating segments from the paths and only
+	// calling the distance function when necessary. If there is no glob the
+	// complexity becomes O(len(a) + len(b)).
+	//
+	// The algorithm works by separating the path into segments delimited by
+	// '/'. We compare the segments in order for a and b, we have three cases:
+	// 1) No segment uses globs, comparison is memcmp of both strings.
+	// 2) One of the strings uses a single "*" or "?". We call the distance
+	//    function only with the segment which reduces the algorithmic
+	//    complexity by reducing the length.
+	// 3) One of the strings uses "**". We need to call distance on the
+	//    the rest of both strings and we can no longer rely on segments.
+	//
+	// Crucially, this optimization works because:
+	// * There are few paths in the releases that use "**", because it results
+	//   in conflict easily. In fact, it is usually used to extract a whole
+	//   directory, meaning the prefix segements should be unique and we can
+	//   avoid computing "**" completely.
+	distance := func(a, b string) bool {
+		a = strings.ReplaceAll(a, "**", "⁑")
+		b = strings.ReplaceAll(b, "**", "⁑")
+		return Distance(a, b, globCost, 1) == 0
 	}
-	if !wildcardSuffixMatch(a, b) {
-		// Fast path.
-		return false
+
+	// Returns the index where the segment ends (next '/' or the end of the
+	// string) and whether the string has a "*" or "?". This function will only
+	// traverse the string once.
+	segmentEnd := func(s string) (end int, hasGlob bool) {
+		end = strings.IndexAny(s, "*?/")
+		if end == -1 {
+			end = len(s) - 1
+		} else if s[end] == '*' || s[end] == '?' {
+			slash := strings.IndexRune(s[end:], '/')
+			if slash != -1 {
+				end = end + slash
+			} else {
+				end = len(s) - 1
+			}
+			hasGlob = true
+		}
+		return end, hasGlob
+	}
+
+	for len(a) > 0 && len(b) > 0 {
+		endA, globA := segmentEnd(a)
+		endB, globB := segmentEnd(b)
+
+		segmentA := a[:endA+1]
+		segmentB := b[:endB+1]
+		if strings.Contains(segmentA, "**") || strings.Contains(segmentB, "**") {
+			// We need to match the rest of the string with the slow path, no
+			// other way around it.
+			return distance(a, b)
+		} else if globA || globB {
+			if !distance(segmentA, segmentB) {
+				return false
+			}
+		} else {
+			if segmentA != segmentB {
+				return false
+			}
+		}
+
+		a = a[endA+1:]
+		b = b[endB+1:]
 	}
 
-	a = strings.ReplaceAll(a, "**", "⁑")
-	b = strings.ReplaceAll(b, "**", "⁑")
-	return Distance(a, b, globCost, 1) == 0
+	// One string is empty, this call is linear.
+	return distance(a, b)
 }
 
 func globCost(ar, br rune) Cost {
 	if ar == '⁑' || br == '⁑' {
 		return Cost{SwapAB: 0, DeleteA: 0, InsertB: 0}
 	}
-	if ar == '/' || br == '/' {
-		return Cost{SwapAB: Inhibit, DeleteA: Inhibit, InsertB: Inhibit}
-	}
 	if ar == '*' || br == '*' {
+		if ar == '*' && br == '/' {
+			return Cost{SwapAB: Inhibit, DeleteA: 0, InsertB: Inhibit}
+		} else if ar == '/' && br == '*' {
+			return Cost{SwapAB: Inhibit, DeleteA: Inhibit, InsertB: 0}
+		}
 		return Cost{SwapAB: 0, DeleteA: 0, InsertB: 0}
 	}
+	if ar == '/' || br == '/' {
+		return Cost{SwapAB: Inhibit, DeleteA: Inhibit, InsertB: Inhibit}
+	}
 	if ar == '?' || br == '?' {
 		return Cost{SwapAB: 0, DeleteA: 1, InsertB: 1}
 	}
 	return Cost{SwapAB: 1, DeleteA: 1, InsertB: 1}
 }
-
-// wildcardPrefixMatch compares whether the prefixes of a and b are equal up
-// to the shortest one. The prefix is defined as the longest substring that
-// starts at index 0 and does not contain a wildcard.
-func wildcardPrefixMatch(a, b string) bool {
-	ai := strings.IndexAny(a, "*?")
-	bi := strings.IndexAny(b, "*?")
-	if ai == -1 {
-		ai = len(a)
-	}
-	if bi == -1 {
-		bi = len(b)
-	}
-	mini := min(ai, bi)
-	return a[:mini] == b[:mini]
-}
-
-// wildcardSuffixMatch compares whether the suffixes of a and b are equal up
-// to the shortest one. The suffix is defined as the longest substring that ends
-// at the string length and does not contain a wildcard.
-func wildcardSuffixMatch(a, b string) bool {
-	ai := strings.LastIndexAny(a, "*?")
-	la := 0
-	if ai != -1 {
-		la = len(a) - ai - 1
-	}
-	lb := 0
-	bi := strings.LastIndexAny(b, "*?")
-	if bi != -1 {
-		lb = len(b) - bi - 1
-	}
-	minl := min(la, lb)
-	return a[len(a)-minl:] == b[len(b)-minl:]
-}
diff --git a/internal/strdist/strdist_test.go b/internal/strdist/strdist_test.go
index 7f8975a0..d337edf8 100644
--- a/internal/strdist/strdist_test.go
+++ b/internal/strdist/strdist_test.go
@@ -58,6 +58,12 @@ var distanceTests = []distanceTest{
 	{f: strdist.GlobCost, r: 1, a: "a**f/hij", b: "abc/def/hik"},
 	{f: strdist.GlobCost, r: 2, a: "a**fg", b: "abc/def/hik"},
 	{f: strdist.GlobCost, r: 0, a: "a**f/hij/klm", b: "abc/d**m"},
+	{f: strdist.GlobCost, r: 1, a: "**a", b: ""},
+	{f: strdist.GlobCost, r: 0, a: "/*foo/", b: "/foo/"},
+	{f: strdist.GlobCost, r: 1, a: "*f", b: ""},
+	{f: strdist.GlobCost, r: 1, a: "", b: "*f"},
+	{f: strdist.GlobCost, r: 0, a: "?**", b: "f/foo"},
+	{f: strdist.GlobCost, r: 0, a: "/aa/a", b: "/a?**"},
 }
 
 func (s *S) TestDistance(c *C) {