Hieracium piloselloides
 
Tall Hawkweed

Several Stems in Ground

22 km North, 3 km East of Hudson Bay
14-June-2016

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Piloselloides: Answers to key questions in Flora of North America leading to this species.  The answers are in the order you would normally work through the key. The points I have considered most important and evident in the photographs are in bold.
bulletCorollas yellow (often each with abaxial red stripe) or orange (drying scarlet to purple); cypselae 1–2.5 mm; pappi of 25–40+, white or sordid bristles in 1 series (plants sometimes stoloniferous); NOT [Corollas yellow or ochroleucous to white (pinkish in H. carneum); cypselae (2–) 2.5–7 mm; pappi of (30–) 40–80, white or stramineous to sordid bristles in 1–2+ series (plants not stoloniferous)]
bulletLeaf blades obovate or oblanceolate to spatulate or lanceolate, lengths (2–) 3–8+ times widths; heads usually (2–) 5–30+ in corymbiform to paniculiform or ± umbelliform arrays, rarely borne singly; NOT [Leaf blades elliptic to ± oblanceolate, lengths 2–4 (–6+) times widths; heads usually borne singly]
bulletCorollas yellow (often each with abaxial red stripe); NOT [Corollas orange (drying scarlet to purple)]
bulletHeads (2–) 10–30+, usually in corymbiform to paniculiform, sometimes ± umbelliform, arrays (rarely borne singly in H. triste); NOT  [Heads (1–) 2–5+, in ± umbelliform arrays]
bulletLeaves usually glabrous, sometimes piloso-hirsute (on midribs and at margins) or scabrellous and/or stipitate-glandular (not both piloso-hirsute and stellate-pubescent); corollas 5–9 mm; NOT [Leaves usually piloso-hirsute and stellate-pubescent; corollas 8–12+ mm]
bulletLeaves glabrous or piloso-hirsute (on midribs and at margins); involucres 5–6 (–7) mm; florets (40–) 60–80+; pappi 3–4 mm; NOT [Leaves glabrous or scabrellous and/or stipitate-glandular; involucres (6–) 7–10 mm; florets 20–60+; pappi 4–5 mm]

 

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Hieracium Answers to key questions in Budd's Flora and Flora of Alberta leading to this genus.  The answers are in the normal botanical descriptive order (e.g. roots, stems, leaves, flowers)
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perennials with fibrous roots; NOT [annuals or taprooted perennials]

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plants with a milky or sticky sap; NOT [sap watery]

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NOT [stem diffusely branched; leaves few, cauline, mostly linear or reduced  to scales]

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plants with leaves all basal or with a few reduced leaves on the stem; NOT [plants with normal stem leaves] (BF)

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plants with at least some cauline leaves, though they may be reduced to bracts; NOT [plants scapose, leaves all basal] (FOA)

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leaves glabrous, or if pubescent, not tomentose; NOT [leaves tomentose ciliate] (BF)

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lower stem and leaves generally long-hairy; NOT [lower stem and leaves generally glabrous, sometimes puberulent, tomentose or hispid] (FOA)

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flower heads several on a flowering stalk; NOT [flower heads solitary on a long stalk]

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bracts in series of 1-3; NOT [bracts in a single series, all equal] (BF)

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involucre of 2 or more series; NOT [involucre uniseriate or biseriate] (FOA)

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bracts with their midribs not thickened

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flowers all ligulate (ray); NOT [some or all of the florets tubular]

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flowers all perfect;  NOT [ligulate flowers when present pistillate or neuter]

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flowers yellow (does not apply to all members of Saskatchewan Hieracium, but does apply to this species)

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stamens united to form a tube around the pistil

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pappus well developed, at least in part of capillary bristles; NOT [pappus of minute scales or none]

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pappus not scale-like at the base, entirely of capillary bristles; NOT [pappus scale-like at the base, with plumose terminal bristles]

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pappus-bristles not plumose

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achenes not flattened; NOT [achenes flattened, at least twice as wide as thick]